Sulfuric Acid → HCID 67917571, compound

Participants

Reaction Steps

A suspenison of 6 (47.41 g, 0.146 mol) in acetonitrile (500 ml) was chilled to -10° C. The cold stirring suspension was treated with 95% H2SO4 (165.5 ml, 3.11 mol) at a rate sufficient to maintain the temperature below 0° C. After equilibrating to room temperature overnight, the resulting solution was poured over ice and was stirred for 4.0 hours. The resulting aqueous suspension was partitioned between 1000 ml and 250 ml of ethyl acetate. The aqueous phase was collected, buffered to pH 8, and partitioned with an additional 50 ml of ethyl acetate. All organic phases were combined and washed with 250 ml of saturated aqueous sodium bicarbonate followed by washing with 250 ml of saturated aqueous sodium chloride. The dried (Na2SO4) organic phase was filtered and concentrated to give 55.27 g (quantitative) of 7 as an orange foam.

Provenance & Evidence