Dimethylformamide → HCID 15042010, compound

Participants

Reaction Steps

A mixture of 0.12 g (0.324 mmol) of tert-butyl [(4R,6S)-6-(iodomethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate, 0.0925 g (0.388 mmol) of 2,6-di-tert-butyl-4-mercaptophenol (See R. J. Laufer, U.S. Pat. No. 3,129,262), 0.067 g (0.49 mmol) of powderly anhydrous potassium carbonate and 0.5 ml of dry N,N-dimethylformamide was stirred for 16 hours at room temperature. The reaction solution was distilled away under reduced pressure. The residue was dissolved in ether, washed with saturated brine solution, dried and distilled away under reduced pressure. The residue was purified by subjecting to silica gel column chromatography [eluent: ethyl acetate-methylene chloride (1:19)]]to give 0.143 g of tert-butyl [(4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-2,2-dimethyl-1,3-dioxane-4-yl]acetate as crystals (yield: 92%). The desired compound was recrystallized from hexane.

Provenance & Evidence