p-Toluenesulfonic acid → HCID 19886006, compound

Participants

Reaction Steps

A solution of 4-(1-acetoxy-4-phenylbutyl)-5-hydroxy-2(5H)-furanone (0.020 g., 0.069 mmol) and p-toluene sulfonic acid (approx. 3 mg.) in 2.5 ml methanol was stirred for 72 hours at room temperature. The reaction mixture was concentrated and partitioned between ethyl ether and water. The organic portion was washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give an oil (0.027 g.) This material was purified by flash chromatography (30% ethyl acetate/hexane) to give a diasteriomeric mixture of the two methoxybutenolides. The mixture was subsequently separated by semi-preparative HPLC on a Whatman Partisil M-9 silica column, with an elution rate of 4 ml/min with 20% ethyl acetate/hexane. One diasteriomer (A) was eluted at 11 minutes, followed by the other (B) at 12 minutes. Concentration gave the purified compounds.

Provenance & Evidence