反应详情

To a solution of 5-fluoronicotinic acid (1.0 g, 7.09 mmol) in THF (10 mL) was added TEA (0.9 mL, 7.73 mmol), followed by ethyl chloroformate (0.6 mL, 7.73 mmol) at 0° C. The reaction was stirred at room temperature 2 h; then it was filtered. The residue was washed with a small amount of THF. The filtrate was chilled to 0° C. and sodium borohydride (0.67 g, 17.73 mmol) was added, followed by dropwise addition of water (5 mL). The reaction was stirred at room temperature overnight. The reaction was partitioned between ethyl acetate and water. The organic layers were combined, dried over sodium sulfate, and concentrated to give a crude product which was used purified by a silica gel chromatography to give (5-fluoropyridin-3-yl)methanol (197 mg, 21.8% yield) as a colorless oil. LCMS retention time 0.375 min; LCMS MH+ 128.

1. filtrationthen it was filtered
2. washThe residue was washed with a small amount of THF
3. temperatureThe filtrate was chilled to 0° C.
4. stirringThe reaction was stirred at room temperature overnight
5. customThe reaction was partitioned between ethyl acetate and water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customto give a crude product which
9. customwas used purified by a silica gel chromatography