Borane;tetrahydrofuran → HCID 70225554, compound

Participants

Reaction Steps

To a solution of (S)-3-cyclohexyllactic acid (15 g) in THF (100 mL) at 0° C. was added 1M BH3-THF (130 mL), and the reaction was warmed to ambient temperature. After 5 h, the reaction was quenched cautiously with aqueous THF (1:1, 100 mL), then with 1M KOH (100 mL). The reaction was concentrated, diluted with water (200 mL), and washed with EtOAc (3×150 mL). The organic extracts were washed with brine (100 mL), dried (MgSO4), filtered and concentrated to give a colorless oil (14 g). 1H NMR (300 MHz, CDCl3) δ0.80-1.04 (m, 2H), 1.05-2.00 (m, 13H), 3.41 (dd, J=10.8, 7.5 Hz, 1H), 3.64 (dd, J=10.8, 2.7 Hz, 1H), 3.84 (m, 1H). MS(CI/NH3) m/e: (M+NH4)+ 176.

Provenance & Evidence