反应详情

温度

-25 °C

To a solution of (−)-B-chlorodiisopinocampheylborane [(−)-DIP-Cl] (25 g, 77.9 mmol) in tetrahydrofuran (90 ml) are added with stirring 3-(2-chloroacetyl)pyridine hydrochloride (Can. J. Chem., vol. 61, p. 334 (1983)) (3.0 g, 15.6 mmol) and triethylamine (2.39 ml, 17.2 mmol) at −25° C., and the reaction mixture is stirred at −25° C. for 3 days. To this mixture is added water (300 ml), and the mixture is warmed to room temperature. To the mixture is added ethyl acetate, and the organic phase is separated. The aqueous phase is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted 6 times with ethyl acetate. The combined organic phase is dried over sodium sulfate, and concentrated under reduced pressure to give yellow oil, which is purified by silica gel column chromatography (methanol/chloroform=1/20) to give the title compound (R)-2-chloro-1-pyridin-3-ylethanol (2.02 g, yield: 82%) as pale yellow oil.

1. temperaturethe mixture is warmed to room temperature
2. customthe organic phase is separated
3. extractionextracted 6 times with ethyl acetate
4. dry with materialThe combined organic phase is dried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customto give yellow oil, which
7. customis purified by silica gel column chromatography (methanol/chloroform=1/20)