3-(2-METHOXY-PHENYL)-PROPAN-1-OL

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Compound 17-1 (2.00 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (3.58 g) and N-bromosuccinimide (2.40 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (2.24 g) as a pale-brown oil. cooling cooling for 1 hr The reaction mixture was washed with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure Diethyl ether (100 ml) was added the precipitated triphenylphosphine oxide was filtered off The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone)

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

Procedure: Meanwhile, a solution of 760 mg of dimethyl sulfoxide in 2 ml of methylene chloride was added dropwise to a solution of 740 mg of oxalyl chloride in 12 ml of methylene chloride at -60° C., with stirring, and the mixture was stirred at the same temperature for 10 minutes. At the end of this time, a solution of 640 mg of 3-(2-methoxyphenyl)propanol (prepared as described above) in 3 ml of methylene chloride was added dropwise to the mixture, and the mixture was stirred for a further 10 minutes. 1.96 g of triethylamine were then slowly added dropwise to the mixture at the same temperature. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes and then mixed with water. The methylene chloride layer was separated, dried over anhydrous magesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 540 mg of 3-(2-methoxyphenyl)propanal as a colorless oil. the mixture was stirred at the same temperature for 10 minutes the mixture was stirred for a further 10 minutes The cooling bath was removed the reaction mixture was stirred at room temperature for 30 minutes mixed with water The methylene chloride layer was separated dried over anhydrous magesium sulfate concentrated by evaporation under reduced pressure The oily residue thus obtained was purified by column chromatography through silica gel by volume mixture of hexane and ethyl acetate as the eluent

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

Procedure: A solution of 980 mg of ethyl 2-methoxycinnamate in 15 ml of tetrahydrofuran was added dropwise to a dispersion of 290 mg of lithium aluminum hydride and 10 ml of tetrahydrofuran, whilst ice-cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours, and then sufficient sodium sulfate decahydrate was slowly added, whilst ice-cooling, to the mixture in order to decompose any excess of the hydride. Insoluble materials were filtered off, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 640 mg of 3-(2-methoxyphenyl)propanol as a colorless oil. cooling After the addition cooling, to the mixture in order Insoluble materials were filtered off the filtrate was concentrated by distillation under reduced pressure The resulting residue was purified by column chromatography through silica gel by volume mixture of hexane and ethyl acetate as the eluent

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

Procedure: A solution of 980 mg of ethyl 2-methoxycinnamate in 15 ml of tetrahydrofuran was added dropwise to a dispersion of 290 mg of lithium aluminum hydride and 10 ml of tetrahydrofuran, whilst ice-cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours, and then sufficient sodium sulfate decahydrate was slowly added, whilst ice-cooling, to the mixture in order to decompose any excess of the hydride. Insoluble materials were filtered off, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 640 mg of 3-(2-methoxyphenyl)propanol as a colorless oil. cooling After the addition cooling, to the mixture in order Insoluble materials were filtered off the filtrate was concentrated by distillation under reduced pressure The resulting residue was purified by column chromatography through silica gel by volume mixture of hexane and ethyl acetate as the eluent

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 3-(2-methoxyphenyl)propanoic acid (1.0 g, 5.55 mmol) was dissolved in THF (27.7 ml). A solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly. The reaction was stirred for about 4 h. Methanol was added and the solvents removed. This process was repeated twice. The solution was passed through a short pad of silica gel with 1:1 ethyl acetate/heptane And then rotovapped to give 3-(2-methoxyphenyl)propan-1-ol (0.946 g, 5.69 mmol, 103% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.19 (dt, 1H), 7.15 (dd, 1H), 6.90 (dt, 1H), 6.86 (d, 1H), 3.84 (s, 3H), 3.60 (t, 2H), 2.73 (t, 2H), −1.92-1.79 (m, 2H), 1.76 (s, 1H), A solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly the solvents removed

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

Procedure: Compound 17-1 (2.00 g) was dissolved in methylene chloride (50 ml), triphenylphosphine (3.58 g) and N-bromosuccinimide (2.40 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 15 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (2.24 g) as a pale-brown oil. cooling cooling for 1 hr The reaction mixture was washed with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure Diethyl ether (100 ml) was added the precipitated triphenylphosphine oxide was filtered off The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone)

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

Procedure: Meanwhile, a solution of 760 mg of dimethyl sulfoxide in 2 ml of methylene chloride was added dropwise to a solution of 740 mg of oxalyl chloride in 12 ml of methylene chloride at -60° C., with stirring, and the mixture was stirred at the same temperature for 10 minutes. At the end of this time, a solution of 640 mg of 3-(2-methoxyphenyl)propanol (prepared as described above) in 3 ml of methylene chloride was added dropwise to the mixture, and the mixture was stirred for a further 10 minutes. 1.96 g of triethylamine were then slowly added dropwise to the mixture at the same temperature. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes and then mixed with water. The methylene chloride layer was separated, dried over anhydrous magesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 540 mg of 3-(2-methoxyphenyl)propanal as a colorless oil. the mixture was stirred at the same temperature for 10 minutes the mixture was stirred for a further 10 minutes The cooling bath was removed the reaction mixture was stirred at room temperature for 30 minutes mixed with water The methylene chloride layer was separated dried over anhydrous magesium sulfate concentrated by evaporation under reduced pressure The oily residue thus obtained was purified by column chromatography through silica gel by volume mixture of hexane and ethyl acetate as the eluent

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

Procedure: A solution of 980 mg of ethyl 2-methoxycinnamate in 15 ml of tetrahydrofuran was added dropwise to a dispersion of 290 mg of lithium aluminum hydride and 10 ml of tetrahydrofuran, whilst ice-cooling. After the addition was complete, the reaction mixture was stirred at room temperature for 1.5 hours, and then sufficient sodium sulfate decahydrate was slowly added, whilst ice-cooling, to the mixture in order to decompose any excess of the hydride. Insoluble materials were filtered off, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 640 mg of 3-(2-methoxyphenyl)propanol as a colorless oil. cooling After the addition cooling, to the mixture in order Insoluble materials were filtered off the filtrate was concentrated by distillation under reduced pressure The resulting residue was purified by column chromatography through silica gel by volume mixture of hexane and ethyl acetate as the eluent