2,2-dimethylbutan-1-ol

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

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

Procedure: 4.4 Grams of a 45% aqueous sodium hydroxide solution, 100 mg of tetrabutylammonium bromide and 5 ml of toluene were mixed, and to the resulting mixture, a solution of 0.7 g of 2,2-dimethylbutanol and 1.72 g of 2-chloromethyl-6-phenoxypyridine in 10 ml of toluene was added at room temperature under a nitrogen atmosphere. After 12 hours, the reaction solution was poured into hydrochloric acid-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was treated by preparative thin layer chromatography (developing solvent, hexane: ethyl acetate=5:1) to obtain 0.45 g of desired 6-phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether [present compound (17)] as an oily product. extracted twice with diethyl ether washed with a saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was treated by preparative thin layer chromatography (developing solvent, hexane: ethyl acetate=5:1)

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

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

Procedure: 4.4 Grams of a 45% aqueous sodium hydroxide solution, 100 mg of tetrabutylammonium bromide and 5 ml of toluene were mixed, and to the resulting mixture, a solution of 0.7 g of 2,2-dimethylbutanol and 1.72 g of 2-chloromethyl-6-phenoxypyridine in 10 ml of toluene was added at room temperature under a nitrogen atmosphere. After 12 hours, the reaction solution was poured into hydrochloric acid-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was treated by preparative thin layer chromatography (developing solvent, hexane:ethyl acetate=5:1) to obtain 0.45 g of desired 6-phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether [present compound (17)] as an oily product. extracted twice with diethyl ether washed with a saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was treated by preparative thin layer chromatography (developing solvent, hexane:ethyl acetate=5:1)

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

Procedure: To a mixture of 4-nitrophenyl chloroformate (1.97 g), 2,2-dimethylbutan-1-ol [CAS No. 1185-33-7] (1 g), and dichloromethane (30 mL), pyridine (1.58 mL) was added, and the resulting mixture was stirred at room temperature for 3 days. To the mixture, ethyl acetate and 1 N hydrochloric acid were added. After shaking the resulting mixture, the organic layer was collected, sequentially washed twice with water and with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (2.23 g). After shaking the resulting mixture the organic layer was collected sequentially washed twice with water and with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate The desiccant was filtered off the filtrate obtained was concentrated under reduced pressure The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate)

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

Procedure: 4.4 Grams of a 45% aqueous sodium hydroxide solution, 100 mg of tetrabutylammonium bromide and 5 ml of toluene were mixed, and to the resulting mixture, a solution of 0.7 g of 2,2-dimethylbutanol and 1.72 g of 2-chloromethyl-6-phenoxypyridine in 10 ml of toluene was added at room temperature under a nitrogen atmosphere. After 12 hours, the reaction solution was poured into hydrochloric acid-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was treated by preparative thin layer chromatography (developing solvent, hexane: ethyl acetate=5:1) to obtain 0.45 g of desired 6-phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether [present compound (17)] as an oily product. extracted twice with diethyl ether washed with a saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure the residue was treated by preparative thin layer chromatography (developing solvent, hexane: ethyl acetate=5:1)