Sodium borohydride → HCID 15541122, compound

Participants

Reaction Steps

To a stirred suspension of sodium borohydride (0.0376 g, 0.00099 mol) in absolute ethanol under nitrogen at room temperature was added in one portion 4-(4′-chloro-biphenyl-4-yl)-4-oxo-butyric acid (0.576 g, 0.00199 mol), and the mixture stirred for 4 hours. Additional sodium borohydride (0.013 g, 0.00034 mol) was added, and the mixture stirred for 18 hours. Additional sodium borohydride (0.0144 g, 0.000381 mol) was added and the mixture stirred for 5 hours. Total reaction time was 27 hours. The reaction was quenched with acetone-water and partitioned between 1 M hydrochloric acid and dichloromethane. The organic layer was washed with brine, dried (Na2SO4), and rotary evaporated. The residue was purified by chromatography on silica gel using dichloromethane-methanol (19:1, 1.3 L; 15:1, 1.3 L) to give 0.101 g of (±)-4-(4′-chloro-biphenyl-4-yl)-4-hydroxy-butyric acid as a white solid; mp 133.5-135.0° C.

Provenance & Evidence