Ethyl Acetate → HCID 59864827, compound

Participants

Reaction Steps

A solution of 1.2 (1.65 g, 4.63 mmol) in ethanol (20 mL) with several drops of concentrated sulfuric acid was heated to reflux overnight. After 16 h, HPLC indicated that no 1.2 remained and the ethanol was removed in vacuo on a rotary evaporator. The concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The separated organic layer was washed with water then brine, stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a dark oil. The desired product was isolated by trituration of the residue with ethyl acetate to yield the desired product as an orange solid. The filtrate from trituration was chromatographed on silica gel, eluting with an ethyl acetate/hexane gradient, to afford additional product. LC-MS ESI (pos.) m/z: 385.0 (M+H).

Provenance & Evidence