Sulfuric Acid → HCID 67809210, compound

Participants

Reaction Steps

A mixture of 422 mg (1.08 mmol) of benzyl rac-α-[[(2-hydroxyl-1,1-dimethylethyl)sulfonyl]methyl]hydrocinnamate, 2 ml (2.2 mmol) of methoxyacetyl chloride and 100 mg (0.8 mmol) of 4-dimethylaminopyridine in 2 ml of pyridine was stirred at 900 for 15 hours. Subsequently, the mixture was poured on to ice and 150 ml of 3N sulphuric acid and extracted three times with 300 ml of ether each time. The organic extracts were then washed with in each case 150 ml of ice-cold 3N sulphuric acid, water, 1M sodium hydrogen carbonate solution and saturated sodium chloride solution, then dried over magnesium sulphate and evaporated under reduced pressure. For purification, the crude product (540 mg of brown oil) was chromatographed on 50 g of silica gel with a 4:1 mixture of toluene and ethyl acetate. There were obtained 180 mg of benzyl rac-α-[[[2-(methoxyacetoxy)-1,1-dimethylethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil, MS: 463 (M+H)+.

Provenance & Evidence