Imidazole → HCID 89748843, compound

Participants

Reaction Steps

A stirred solution of allylic alcohol 66 (3.00 g, 18.5 mmol) in CH2Cl2 (53 ml) was cooled to 0° C. Imidazole (2.27 g, 33.3 mmol) was added in one portion followed by t-butylchlorodimethylsilane (3.34 g, 22.2 mmol). The cooling bath was removed and the reaction mixture stirred at r.t. for 16 h before being poured into 10% aq. HCl (100 ml). The mixture was extracted with 40/60 petroleum ether (2×100 ml). The combined organics were washed with saturated NaCl solution (100 ml), dried (MgSO4), filtered, and concentrated to give the crude material. This was purified by column chromatography, eluting with 40/60 petroleum ether, to give the protected alcohol 67 (4.68 g, 92%) as a colourless liquid. The 1H NMR data and optical rotation matched that reported in the literature (Uenishi, J. i. et al., Organic Letters 2011, 13, 2350).

Provenance & Evidence