3-diazooxolan-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Propane-1,3-diol (0.050 g, 0.657 mmol) was dissolved in dichloromethane (6.5 mL) and treated with rhodium (II) acetate (3 mg) then solution was heated to reflux. One third of a solution (ca. 2 mL) of 3-diazodihydrofuran-2(3H)-one (0.283 g, 0.986 mmol) dissolved in a mixture of dichloromethane (3 mL) and diethyl ether (2.5 mL) was added dropwise to the hot solution then the solution was heated at reflux for 30 minutes. The solution of 3-diazodihydrofuran-2(3H)-one was added in two portions (ca. 2 mL each) to the refluxing mixture in a similar manner. The reaction was cooled to ambient temperature and concentrated in vacuo. The crude oil was chromatographed on silica gel eluting with ethyl acetate/hexanes (2:1). 3-(3-Hydroxypropoxy)dihydrofuran-2(3H)-one was recovered as a colorless oil (47 mg, 45%). solution was heated to reflux was added dropwise to the hot solution the solution was heated at reflux for 30 minutes concentrated in vacuo The crude oil was chromatographed on silica gel eluting with ethyl acetate/hexanes (2:1) 3-(3-Hydroxypropoxy)dihydrofuran-2(3H)-one was recovered as a colorless oil (47 mg, 45%)