Diethyl Ether → HCID 13576506, compound

Participants

Reaction Steps

A solution of 5.14 g of m-chloroperoxybenzoic acid (85%) in 125 ml CH2Cl2 was added dropwise to a solution of 7.5 g of 5-phenylthiomethyl-3-(4-toluoyl)-1,2,4-oxadiazole in 150 ml CH2Cl2 at -70° under N2. The temperature was maintained below -65° during the addition by controlling the addition rate and stirring was continued for 30 minutes after the addition while maintaining the temperature below -65°. The resulting mixture was poured directly into a separatory funnel containing 250 ml of 10% Na2S2O3 and 500 ml of Et2O. The organics were washed with saturated NaHCO3 and dried over MgSO4. Concentration gave an oil which solidified on standing. Recrystallization from acetone/hexane gave 5.3 g (64%) of needles, m.p. 97°-99°.

Provenance & Evidence