Acetyl chloride → HCID 67791890, compound

Participants

Reaction Steps

4,6-Bis(tert-butyldimethylsilyloxy)-5-hydroxy-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole (401 mg) was dissolved in 20 ml of methylene chloride. Five milliliters of triethylamine and 0.5 g of 4-dimethylaminopyridine were added, and 100 mg of acetyl chloride was then added, followed by stirring the mixture overnight at room temperature. The reaction mixture was diluted with diethyl ether, and washed with dilute hydrochloric acid, a sodium hydrogen carbonate aqueous solution and a sodium chloride aqueous solution in sequence. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 355 mg of 5-acetoxy-4,6-bis(tert-butyldimethylsilyloxy)-3,3a,4,5,6,7-hexahydro-2,1-benzoisooxazole having the following property (yield 80%).

Provenance & Evidence