Toluene → HCID 86676172, compound

Participants

Reaction Steps

To a solution of 38 (500 mg, 1.7 mmol) in THF (25 mL) was added 1.6M DIBALH in toluene (3.1 mL, 5.01 mmol) at −78° C. and stirred for 3 h at the same temperature. The reaction mixture was quenched with water (20 mL), extracted with EtOAc (2×50 mL), the combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated. The crude compound was purified by silica gel column chromatography (100-200 mesh, eluted with 20% EtOAc/pet-ether) to obtain compound 39 (350 mg, 69%) as a brown solid. Rf: 0.5 (40% EtOAc/pet-ether); (m/z): 303 [MH]+; 1H NMR (400 MHz, CDCl3): δ 9.85 (1H, S), 8.27 (1H, d, J=2.8 Hz), 7.79 (1H, d, J=8.8 Hz), 7.38-7.20 (10H, m), 7.03 (1H, dd, J=3.2, 8.8 Hz), δ 4.77 (4H, s).

Provenance & Evidence