Ethyl Acetate → [1-(2,5-Dichlorophenyl)-cyclopentyl]-methanol

Participants

Reaction Steps

A solution of 1-(2,5-dichlorophenyl)-cyclopentanecarbaldehyde (199) (25 g, 103.305 mmol) in methanol (300 mL), was cooled in ice bath, NaBH4 (7.816 g, 206.612 mmol) was added portion-wise and the mixture was stirred for 3 h at room temperature. Silica thin layer chromatography was performed (10% ethyl acetate in hexane, Rf=0.5). After completion of the reaction, it was quenched with saturated NH4Cl solution (100 mL), methanol was removed from the reaction mixture under reduced pressure, the residue was diluted with water and the mixture was extracted with dichloromethane, the combined organic layer was washed with brine, dried, and concentrated. The concentrate was purified using normal silica gel (100-200 mesh) column chromatography using a gradient eluent of 2 to 10% ethyl acetate in hexane to get [1-(2,5-dichlorophenyl)-cyclopentyl]-methanol (200) (23 g, 90.82%) as a colorless liquid.

Provenance & Evidence