Sodium borohydride → 1-(p-Chlorophenyl)cyclopentanemethanol

Participants

Reaction Steps

To a stirred solution of 1-(4-chlorophenyl)-cyclopentanecarbaldehyde (318) (19 g, 91.06 mmol) in methanol (250 mL) was added NaBH4 (6.9 g, 182.13 mmol) portion-wise at 0° C. and the reaction mixture was stirred at room temperature for 2 h. After completion of the reaction, the reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (20 mL). The methanol was removed and the residue was diluted with water (100 mL). The mixture was extracted with ethyl acetate (3×100 mL) and the combined organic parts were dried and concentrated. The crude product was purified by silica CombiFlash column (5% ethyl acetate in hexane was used as eluent) to get [1-(4-chlorophenyl)-cyclopentyl]-methanol (319) (13.3 g, 69%) as a colourless oil.

Provenance & Evidence