Imidazole → HCID 68492781, compound

Participants

Reaction Steps

239 (183 mg, 0.83 mmol), TIPS-Cl (237 mg, 3.5 mmol) and imidazole (237 mg, 3.5 mmol) in DCM (10 ml) were stirred at rt for 24 h. The reaction mixture was quenched with water (5 ml) and extracted with DCM (3×10 ml). The combined organic extracts were washed with brine (10 ml), dried (MgSO4) and concentrated in vacuo. Purification (personal flashmaster: 20 g, EtOAc:MeOH:TEA; 100:10:1) afforded the title compound (332 mg) as a yellow oily solid. 1H NMR (270 MHz; CDCl3) 1.07 (18H, d, J=6.4 Hz, 6×CH3CH), 1.08 (3H, s, CH3), 1.15-1.28 (3H, m, 3×CHCH3), 1.25 (3H, s, CH3), 1.21 (3H, d, J=6.4 Hz, CH3CH), 2.44 (1H, d, J=15.8 Hz, CHH), 2.65 (1H, d, J=15.8 Hz, CHH), 3.74 (3H, s, OCH3), 4.0 (1H, q, J=6.4 Hz, CHCH3), 6.46 (1H, s, CH), 6.67 (1H, s, CH). LC/MS (ES+) tr=1.8 min, m/z 378.24 (M++H).

Provenance & Evidence