(E)-4-phenylmethoxybut-2-en-1-ol

Conditions: temp:-23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 190 ml of dry dichloromethane, 3.3 g of a molecular sieves (powder, 3A) was suspended, and 4.2 ml of isopropyl orthotitanate and 2.9 ml of diethyl L(+)-tartarate were added thereto under stirring at -23° C. The mixture was stirred at the same temperature for 15 minutes. Then, 3 ml of a dry dichloromethane solution of 4.7 g of (E)-4-benzyloxy-2-buten-1-ol was added thereto, and the mixture was stirred at the same temperature for 5 minutes. 11 ml of tert-butylhydroxyperoxide (5.17M dichloromethane solution) was added thereto, and the mixture was stirred for further seven hours. Then, the reaction solution was left to stand at -23° C. overnight. To the reaction solution, 190 ml of diethyl ether and 4.2 ml of a saturated sodium sulfate aqueous solution were added, and the mixture was stirred at room temperature for 4 hours. The insolubles were removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in 240 ml of diethyl ether, and 42 ml of a 1N sodium chloride aqueous solution was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes. The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 2.9 g of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol as colorless oily substance. The mixture was stirred at the same temperature for 15 minutes the mixture was stirred at the same temperature for 5 minutes the mixture was stirred for further seven hours Then, the reaction solution was left the mixture was stirred at room temperature for 4 hours The insolubles were removed by filtration the solvent was distilled off under reduced pressure The residue was dissolved in 240 ml of diethyl ether 42 ml of a 1N sodium chloride aqueous solution was added under stirring at 0° C The mixture was stirred at 0° C. for 30 minutes The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure 2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance. The mixture was stirred at 0° C. for 1.5 hours extracted with ethyl acetate The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate Then, the solvent was distilled off under reduced pressure the residue was subjected to distillation under reduced pressure 2.0 mmHg, 142° C.)

Conditions: temp:-23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 190 ml of dry dichloromethane, 3.3 g of a molecular sieves (powder, 3A) was suspended, and 4.2 ml of isopropyl orthotitanate and 2.9 ml of diethyl L(+)-tartarate were added thereto under stirring at -23° C. The mixture was stirred at the same temperature for 15 minutes. then, 3 ml of a dry dichloromethane solution of 4.7 g of (E)-4-benzyloxy-2-buten-1-ol was added thereto, and the mixture was stirred at the same temperature for 5 minutes. 11 ml of tert-butylhydroxyperoxide (5.17M dichloromethane solution) was added thereto, and the mixture was stirred for further seven hours. Then, the reaction solution was left to stand at -23° C. overnight. To the reaction solution, 190 ml of diethyl ether and 4.2 ml of a saturated sodium sulfate aqueous solution were added, and the mixture was stirred at room temperature for 4 hours. The insolubles were removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in 240 ml of diethyl ether, and 42 ml of a 1N sodium chloride aqueous solution was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes. The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane,/ethyl acetate=1/1) to obtain 2.9 g of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol as colorless oily substance. The mixture was stirred at the same temperature for 15 minutes the mixture was stirred at the same temperature for 5 minutes the mixture was stirred for further seven hours Then, the reaction solution was left the mixture was stirred at room temperature for 4 hours The insolubles were removed by filtration the solvent was distilled off under reduced pressure The residue was dissolved in 240 ml of diethyl ether 42 ml of a 1N sodium chloride aqueous solution was added under stirring at 0° C The mixture was stirred at 0° C. for 30 minutes The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (n-hexane,/ethyl acetate=1/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance. The mixture was stirred at 0° C. for 1.5 hours extracted with ethyl acetate The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate Then, the solvent was distilled off under reduced pressure the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.)

Conditions: temp:-23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 190 ml of dry dichloromethane, 3.3 g of a molecular sieves (powder, 3A) was suspended, and 4.2 ml of isopropyl orthotitanate and 2.9 ml of diethyl L(+)-tartarate were added thereto under stirring at -23° C. The mixture was stirred at the same temperature for 15 minutes. Then, 3 ml of a dry dichloromethane solution of 4.7 g of (E)-4-benzyloxy-2-buten-1-ol was added thereto, and the mixture was stirred at the same temperature for 5 minutes. 11 ml of tert-butylhydroxyperoxide (5.17M dichloromethane solution) was added thereto, and the mixture was stirred for further seven hours. Then, the reaction solution was left to stand at -23° C. overnight. To the reaction solution, 190 ml of diethyl ether and 4.2 ml of a saturated sodium sulfate aqueous solution were added, and the mixture was stirred at room temperature for 4 hours. The insolubles were removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in 240 ml of diethyl ether, and 42 ml of a 1N sodium hydroxide aqueous solution was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes. The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 2.9 g of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol as colorless oily substance. The mixture was stirred at the same temperature for 15 minutes the mixture was stirred at the same temperature for 5 minutes the mixture was stirred for further seven hours Then, the reaction solution was left the mixture was stirred at room temperature for 4 hours The insolubles were removed by filtration the solvent was distilled off under reduced pressure The residue was dissolved in 240 ml of diethyl ether 42 ml of a 1N sodium hydroxide aqueous solution was added under stirring at 0° C The mixture was stirred at 0° C. for 30 minutes The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance. The mixture was stirred at 0° C. for 1.5 hours extracted with ethyl acetate The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate Then, the solvent was distilled off under reduced pressure the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance. The mixture was stirred at 0° C. for 1.5 hours extracted with ethyl acetate The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate Then, the solvent was distilled off under reduced pressure the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.)

Conditions: temp:-23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 190 ml of dry dichloromethane, 3.3 g of a molecular sieves (powder, 3A) was suspended, and 4.2 ml of isopropyl orthotitanate and 2.9 ml of diethyl L(+)-tartarate were added thereto under stirring at -23° C. The mixture was stirred at the same temperature for 15 minutes. Then, 3 ml of a dry dichloromethane solution of 4.7 g of (E)-4-benzyloxy-2-buten-1-ol was added thereto, and the mixture was stirred at the same temperature for 5 minutes. 11 ml of tert-butylhydroxyperoxide (5.17M dichloromethane solution) was added thereto, and the mixture was stirred for further seven hours. Then, the reaction solution was left to stand at -23° C. overnight. To the reaction solution, 190 ml of diethyl ether and 4.2 ml of a saturated sodium sulfate aqueous solution were added, and the mixture was stirred at room temperature for 4 hours. The insolubles were removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in 240 ml of diethyl ether, and 42 ml of a 1N sodium chloride aqueous solution was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes. The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 2.9 g of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol as colorless oily substance. The mixture was stirred at the same temperature for 15 minutes the mixture was stirred at the same temperature for 5 minutes the mixture was stirred for further seven hours Then, the reaction solution was left the mixture was stirred at room temperature for 4 hours The insolubles were removed by filtration the solvent was distilled off under reduced pressure The residue was dissolved in 240 ml of diethyl ether 42 ml of a 1N sodium chloride aqueous solution was added under stirring at 0° C The mixture was stirred at 0° C. for 30 minutes The diethyl ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto under stirring at 0° C. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure 2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance. The mixture was stirred at 0° C. for 1.5 hours extracted with ethyl acetate The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate Then, the solvent was distilled off under reduced pressure the residue was subjected to distillation under reduced pressure 2.0 mmHg, 142° C.)

Conditions: temp:-23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.3 g of molecular sieve (powder, 3A) was suspended in 190 ml of dry dichloromethane, and 4.2 ml of isopropyl orthotitanate and 2.9 ml of diethyl L(+)-tartrate were added thereto at -23° C. under stirring. The mixture was stirred at the same temperature for 15 minutes. Then, 3 ml of a dry dichloromethane solution of 4.7 g of (E)-4-benzyloxy-2-buten-1-ol was added thereto, and the mixture was stirred at the same temperature for 5 minutes. 11 ml of tert-butylhydroperoxide (a 5.17M dichloromethane solution) was added thereto, and the mixture was stirred for further 7 hours. Then, the reaction mixture was left to stand at -23° C. overnight. 190 ml of diethyl ether and 4.2 ml of a saturated sodium sulfate aqueous solution were added to the reaction solution, and the mixture was stirred at room temperature for 4 hours. Insolubles were removed by filtration, and then the solvent was distilled off under reduced pressure. The residue was dissolved in 240 ml of diethyl ether. 42 ml of a 1N sodium hydroxide aqueous solution was added thereto at 0° C. under stirring, and the mixture was stirred at 0° C. for 30 minutes. The ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 2.9 g of (2S, 3S)-4-benzyloxy-2,3-epoxy-1-butanol as colorless oily substance. The mixture was stirred at the same temperature for 15 minutes the mixture was stirred at the same temperature for 5 minutes the mixture was stirred for further 7 hours Then, the reaction mixture was left the mixture was stirred at room temperature for 4 hours Insolubles were removed by filtration the solvent was distilled off under reduced pressure The residue was dissolved in 240 ml of diethyl ether 42 ml of a 1N sodium hydroxide aqueous solution was added at 0° C. under stirring the mixture was stirred at 0° C. for 30 minutes The ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g of (Z)-4-benzyloxy-2-butenal was dissolved in 60 ml of ethanol, and 850 mg of sodium borohydride was added thereto at 0° C. under stirring. The mixture was stirred at 0° C. for 1.5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.) to obtain 2.2 g of (E)-4-benzyloxy-2-buten-1-ol as colorless oily substance. The mixture was stirred at 0° C. for 1.5 hours extracted with ethyl acetate The ethyl acetate solution was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate Then, the solvent was distilled off under reduced pressure the residue was subjected to distillation under reduced pressure (2.0 mmHg, 142° C.)

Conditions: temp:-23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.3 g of molecular sieve (powder, 3A) was suspended in 190 ml of dry dichloromethane, and 4.2 ml of isopropyl orthotitanate and 2.9 ml of diethyl L(+)-tartrate were added thereto at -23° C. under stirring. The mixture was stirred at the same temperature for 15 minutes. Then, 3 ml of a dry dichloromethane solution of 4.7 g of (E)-4-benzyloxy-2-buten-1-ol was added thereto, and the mixture was stirred at the same temperature for 5 minutes. 11 ml of tert-butylhydroperoxide (a 5.17M dichloromethane solution) was added thereto, and the mixture was stirred for further 7 hours. Then, the reaction mixture was left to stand at -23° C. overnight. 190 ml of diethyl ether and 4.2 ml of a saturated sodium sulfate aqueous solution were added to the reaction solution, and the mixture was stirred at room temperature for 4 hours. Insolubles were removed by filtration, and then the solvent was distilled off under reduced pressure. The residue was dissolved in 240 ml of diethyl ether. 42 ml of a 1N sodium hydroxide aqueous solution was added thereto at 0° C. under stirring, and the mixture was stirred at 0° C. for 30 minutes. The ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to obtain 2.9 g of (2S, 3S)-4-benzyloxy-2,3-epoxy-1-butanol as colorless oily substance. The mixture was stirred at the same temperature for 15 minutes the mixture was stirred at the same temperature for 5 minutes the mixture was stirred for further 7 hours Then, the reaction mixture was left the mixture was stirred at room temperature for 4 hours Insolubles were removed by filtration the solvent was distilled off under reduced pressure The residue was dissolved in 240 ml of diethyl ether 42 ml of a 1N sodium hydroxide aqueous solution was added at 0° C. under stirring the mixture was stirred at 0° C. for 30 minutes The ether layer was washed sequentially with a saturated sodium hydrogencarbonate aqueous solution and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)