Imidazole → HCID 53957647, compound

Participants

Reaction Steps

3-Ethynyl-3-hydroxyquinuclidine (1.5 g) and imidazole (1.7 g) were stirred in dimethyl formamide (25 ml). Trimethylsilylchloride (1.35 g) was added slowly to the solution and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was poured into water (150 ml) and the aqueous phase extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were combined, washed with water (2×100 ml), brine (100 ml), dried (MgSO4) and evaporated to give 3-ethynyl-3-trimethylsilyloxyquinuclidine as an oil (1.8 g), NMR: 0.15 (9H, s), 1.2-1.38 (1H, m), 1.42-1.6 (1H, m), 1.65-1.9 (3H, m), 2.55-2.7 (4H, m), 2.76 (1H, d), 3.02 (1H, d), 3.55 (1H, s), m/z 224 (M+H).

Provenance & Evidence