Methanol → [2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

Participants

Reaction Conditions

Reaction Steps

2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde (30 gm) was added methanol (30 ml) and tetrahydrofuran (270 ml) at room temperature. The reaction mixture was then cooled to 0° C. and then added sodium borohydride (5.8 gm) for 30 minutes at 0 to 5° C. The reaction mass was stirred for 1 hour 30 minutes and then added water (150 ml) and ethyl acetate (150 ml). The reaction mass was stirred for 10 minutes, and then the layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate and then concentrated to obtain a residual solid. To the residual solid was added n-hexane (150 ml) and stirred for 30 minutes. The separated solid was filtered and dried to obtain 29 gm of (2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol.

Provenance & Evidence