Imidazole → HCID 68495874, compound

Participants

Reaction Steps

To a solution of 224 (1.25 g, 6 mmol) in DCM (50 ml) was added imidazole (1.73 g, 25.4 mmol) and triisopropylsilyl chloride (2.71 ml, 12.7 mmol). The reaction mixture was stirred at rt for 22 h. Water (30 ml) and Chloroform (30 ml) were added. The layers separated and the aqueous layer extracted with chloroform (3×30 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo. Purification by column chromatography eluting with EtOAc:MeOH:TEA; 10:1:01 afforded the title compound (1.78 g, 81%) as colourless oil. 1H NMR (270 MHz; CDCl3) 1.06 (18H, d, J=6.7 Hz, 6×CH3CH), 1.14 (6H, s, 2×CH3), 1.14-1.28 (3H, m, 3×CH), 2.51 (2H, s, CH2), 3.74 (3H, s, OCH3), 3.89 (2H, s, CH2), 6.46 (1H, s, CH), 6.51 (1H, s, CH). 13C NMR (67.5 MHz; CDCl3) 12.95 (CH3), 18.03 (CH3), 27.76 (CH), 41.17 (CH2), 43.97 (CH2), 48.78 (C(CH3)2), 55.56 (OCH3), 112.96 (CH), 117.39 (CH), 126.24 (C), 126.92 (C), 143.58 (C), 149.34 (C). LC/MS (ES+) tr=2.65 min, m/z 364.36 (M++H).

Provenance & Evidence