Imidazole → HCID 53897948, compound

Participants

Reaction Steps

To a stirred and ice-cooled solution of 8 (4.05 g, 15.9 mmol) and imidazole (2.16 g, 31.7 mmol) in N,N-dimethylformamide was added chlorotriethylsilane (4 mL, 23.8 mmol), and the mixtrue was stirred at ambient temperature overnight. To the mixture was added ice and diethyl ether and the mixture was stirred at ambient temperature for 20 min. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 7.40 g of an oily material, which was purified by column chromatography (silica gel 70 g, 4-12% ethyl acetate in n-hexane) to give 5.89 g (quantitative) of 9, as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ: 0.55 (6H, q, J=7.9 Hz), 0.80(2H, dd, J=6.8 and 4.2 Hz), 0.91(9H, t, J=7.9 Hz), 0.92(2 H), 1.20 (6H, s), 3.39(2H, s), 7.55(2H, t, J=7.4 Hz), 7.64(1H, t, J=7.4 Hz), 7.89(2H, d, J=7.4 Hz)

Provenance & Evidence