Dimethyl Sulfide → HCID 86745884, compound

Participants

Reaction Steps

Prepared according to the method described, in a vessel equipped with a CO2 condenser and kept under N2, starting from 6.8 g (0.054 mmol) of (CH3)2SO4, 3.3 g of (CH3)2S, 6 ml of THF (tetrahydrofuran), 8 ml of DMSO and 1.7 g (0.054 mol) of 75% NaH in mineral oil. (+)-(5S)-5-Ethyl-2,6,6-trimethyl-2-cyclohexen-1-one (6.6 g, 0.033 mol, [α]20D =+82.4°) in 2 ml of DMSO was added at ~6°. The mixture was stirred over the week-end and then 21 ml of ethyl acetate were added, followed by 21 ml of water added dropwise. After the usual treatment and distillation on residues, a mixture containing 54% of the desired product was obtained. The desired epoxide was separated from the mixture by further distillation.

Provenance & Evidence