Imidazole → (R)-1-Cyclohexyl-1-phenyl-1-trimethylsiloxy-2-propanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 12 ml (95 mmoles) of trimethylsilyl chloride and 11.6 g (172 mmoles) of imidazole in 100 ml of DMF was added 20 g (86 mmoles) of (R)-1-cyclohexyl-1-hydroxy-1-phenyl-2-propanone. This mixture was heated to 85° C. overnight. The next day, the mixture was cooled and poured onto a mixture of 100 ml of petroleum ether and 100 ml of ether. This was extracted with water. The organic layer was separated, dried, and the solvent removed. The residue was chromatographed on silica gel with hexane as the eluent to give 18.0 g of clear oil. IR 2950, 1730 cm-1NMR (CDCl3) δ7.4(m, 5H), 2.3(t, 1H), 2.1(s, 3H), 1.9-1.0(m, 10H), 0.3(s, 9H).

Provenance & Evidence