Sodium borohydride → [3-Fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol

Participants

Reaction Steps

3-Fluoro-5-(4-methoxy-benzylamino)-benzaldehyde (crude product) was dissolved in anhydrous ethanol (40 ml) and cooled in an ice bath. Sodium borohydride (800 mg, 21 mmol) was then added with stirring. After 1 hr., the mixture was diluted with methanol and excess ammonium chloride was added. After stirring for 1 hr. at room temperature, the mixture was evaporated in vacuo and coevaporated with methanol several times. The residue was purified by silica gel column chromatography (eluent, EA: hexane (from 1:4 to 1:1)) to afford 2.16 g (39%) of [3-fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol as a white solid. m.p. 93° C.

Provenance & Evidence