Sodium borohydride → 1-(p-Chlorophenyl)cyclopentanemethanol

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.

1. customAfter completion of the reaction
2. customthe reaction mixture was quenched with a saturated aqueous solution of ammonium chloride (20 mL)
3. customThe methanol was removed
4. additionthe residue was diluted with water (100 mL)
5. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
6. customthe combined organic parts were dried
7. concentrationconcentrated
8. customThe crude product was purified by silica CombiFlash column (5% ethyl acetate in hexane was used as eluent)

ORD record

ord-fabaedbab3e847568211ece6cedc66ba

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2