Sodium borohydride → 2-Chloro-alpha-methyl-4-pyridinemethanol

1-(2-Chloropyridin-4-yl)ethan-1-one (110 g, 707 mmol, 1.00 equiv) and methanol (1500 mL) were added to a 3000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen. NaBH4 (26.4 g, 698 mmol, 1.00 equiv) was added in portions at 0° C. The reaction mixture was stirred overnight at room temperature. The reaction was then quenched by the addition of water (1000 mL). The resulting mixture was concentrated under vacuum and extracted with dichloromethane (3×2000 mL). The combined organic layer was washed with brine (2×2000 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel (1:5 ethyl acetate/petroleum ether) to afford 1-(2-chloropyridin-4-yl)ethan-1-ol as colorless oil.

1. custompurged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customThe reaction was then quenched by the addition of water (1000 mL)
4. concentrationThe resulting mixture was concentrated under vacuum
5. extractionextracted with dichloromethane (3×2000 mL)
6. washThe combined organic layer was washed with brine (2×2000 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum
9. customThe residue was purified by column chromatography on silica gel (1:5 ethyl acetate/petroleum ether)

ORD 기록

ord-779508f626fb4bf9bb11058052928967

출처 데이터셋

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09242984B2