Lithium tri-s-butylborohydride → HCID 88875568, compound

Participants

Reaction Steps

To a solution of 31 (1.30 g, 5 mmol) in hexanes (30 mL) which was cooled down to −78° C. under N2, L-selectride (20 mL, 10 mmol) was added dropwise. The resulting mixture was further stirred at this temperature for 1 h, and then quenched with brine and diluted with EtOAc (100 mL). The organic layers were washed with brine, dried, and evaporated. The obtained residue was chromatographed on silica gel eluted with EtOAc/hexanes (0-20%) to obtain 0.80 g (31%) of 32 as a yellowish oil. NMR (CD3OD) δ 1.21 (3 H, s), 1.22 (3 H, s), 3.68 (1 H, dd, J=6.36, 8.36 Hz), 3.84 (1 H, dd, J=6.78, 8.52 Hz), 4.00 (1 H, m), 4.23 (1 H, m), 4.70 (1 H, d, J=5.04 Hz), 7.68 (1 H, dd, J=1.52, 9.20 Hz), 8.15 (1 H, d, J=1.96 Hz); LC/MS (M+1) 262.

Provenance & Evidence