Imidazole → HCID 5461810, compound

Participants

Reaction Steps

To a solution of (S)-3-cyclohexyl-1-propyn-3-ol, (obtained according to Preparation 7.A. and 8.A. (2.76 g, 0.02 mol), in 10 ml N,N-dimethylformamide (DMF), cooled to 0° C., was added imidazole (2.1 g), followed by tertbutyldimethylchlorosilane (3.1 g, 0.02 mol). The mixture was stirred for 3 h. Water (80 ml) and hexane (80 ml) were added; the organic layer was separated and combined with 2×80 ml of hexane extractions of the aqueous layer. The solvent was removed (in vacuo), after drying over sodium sulfate, to give a crude residue (4.3 g) which was chromatographed on silica gel (80 g), eluting with ethyl acetate-hexane (2:1, v/v) to afford 3-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-yne.

Provenance & Evidence