3-Methoxyacetophenone → 2-(3-Methoxyphenyl)-2-methyloxirane

Participants

Reaction Conditions

Reaction Steps

Trimethyloxosulphonium iodide (100 g, 0.45 mole) was added as a slurry in dimethylsulphoxide (100 ml) to a stirred cooled suspension of sodium hydride (22.6 g of a 50% dispersion of oil, washed free from oil with ether) under nitrogen, keeping the internal temperature at 20° C. by ice-cooling. After stirring at room temperature for 1 hour 3-methoxyacetophenone (45 g, 0.3 mole) was added in a 1:1 mixtures of dry tetrahydrofuran-dimethylsulphoxide (100 ml). The reaction mixture was slowly heated to 50° C. over 1 hour and this temperature was maintained for 1 hour. The mixture was cooled, poured on to ice water and extracted with ether (4×150 ml). The combined extracts were washed with brine, dried (MgSO4) and evaporated to an oil (34.0 g) and used crude for the preparation of (3-methoxy)-α-methyl-α[(methylamino)methyl]benzene methanol.

Provenance & Evidence