m-Chloroperbenzoic acid → 2-(Trimethylsilyl)furo[3,2-B]pyridine 4-oxide

Participants

Reaction Steps

A solution of m-CPBA (17 g, 0.098 mmol) in DCM (80 ml) is added to a solution of 2-(Trimethylsilyl)furo(3,2-b)pyridine (7.5 g, 0.0392 mol) in dry DCM (50 ml) at 0° C. The reaction mixture is stirred at RT for 4 h and then diluted with DCM (100 ml), washed with saturated sodium bicarbonate (2×100 ml) and saturated brine (50 ml), dried over sodium sulphate and evaporated to afford the title compound as (6 g, 73.5%) light brown oil. TLC: chloroform/methanol (9/1): Rf=0.8; 1H NMR (DMSO-d6, 400 MHz) δ [ppm] 8.21-8.19 (1H, d, J1=6.4 Hz), 7.693-7.671 (1H, d, J1=8.52 Hz), 7.465-7.163 (1H, d, J1=1 Hz), 7.333-7.296 (1H, dd, J1=6.36 Hz, J2=8.48 Hz), 0.372-0.355 (9H, s).

Provenance & Evidence