Ethyl Acetate → (1-Naphthalen-1-yl-cyclopentyl)-methanol

Participants

Reaction Steps

A solution of 1-naphthalen-1-yl-cyclopentanecarbaldehyde (339) (10 g, 44.6 mmol) in methanol (150 mL) was cooled to 0° C. and NaBH4 (3.373 g, 89.2 mmol) was added in portions (8 portions). After the addition was completed the reaction mixture was allowed to stir at room temperature for 1 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.3). The reaction mixture was quenched with aqueous NH4Cl solution and concentrated in vacuo as much as possible; diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic part was washed with brine (50 mL), dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using gradient eluent mixture of ethyl acetate and hexane to get pure (1-naphthalen-1-yl-cyclopentyl)-methanol (340) (8.75 g, 87%) as a white solid.

Provenance & Evidence