Imidazole → HCID 11099363, compound

Participants

Reaction Steps

t-Butyldimethylsilyl chloride (4.02 g, 26.67 mmol) in CH2Cl2 (25 ml) was added to a solution of N,N-dimethyl-4-hydroxy-1,3-benzodioxole-5-carboxamide (5) (4.49 g, 20.5 mmol) and imidazole (3.63 g, 53.3 mmol) in CH2Cl2 (25 ml). The solution was stirred for 3 h at rt, during which time a white solid precipitated. The mixture was washed with brine, dried over MgSO4 and concentrated. Chromatography on silica (hexane/ethyl acetate, 1:1) afforded 9 (5.44 g, 82%) as a crystalline solid. 1H NMR (270 MHz, CDCl3) ε 6.75 (d, J=8.0 Hz, 1H), 6.50 (d, J=8.0 Hz, 1H), 5.92 (s, 2H), 3.03 (s, 3H), 2.87 (s, 3H), 0.94 (s, 9H), 0.16 (bs, 6H). 13C NMR (100 MHz, CDCl3) ε 168.9 (C), 149.3 (C), 137.0 (C), 135.5 (C), 124.9 (C), 121.4 (CH), 102.8 (CH), 101.0 (CH2), 38.2 (CH3), 34.9 (CH3), 25.4 (3CH3), 18.1 (C), -4.6 (2CH3).

Provenance & Evidence