Sodium borohydride → (3-Fluoropyridin-2-yl)methanol

A solution of 2-formyl-3-fluoropyridine (4.0 g, 32 mmol) and sodium borohydride (309 mg, 8 mmol) in absolute ethanol (40 mL) was stirred at 0° C. for 15 minutes and at room temperature for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (5 mL) and filtered through diatomaceous earth to remove solids. The filtrate was evaporated and the resultant white solid was dissolved in ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (5×30 mL) and the combined extracts were dried over anhydrous sodium sulfate. Solvent removal provided 3.78 g (93%) of the titled product as a pale yellow oil:

1. customThe reaction was quenched with saturated aqueous ammonium chloride (5 mL)
2. filtrationfiltered through diatomaceous earth
3. customto remove solids
4. customThe filtrate was evaporated
5. dissolutionthe resultant white solid was dissolved in ethyl acetate
6. extractionThe aqueous layer was extracted with ethyl acetate (5×30 mL)
7. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
8. customSolvent removal

ORD-Eintrag

ord-fdf34a2ef3d04e6db937db8c77af126e

Quelldatensatz

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05593993