p-Toluenesulfonic acid → 5-t-Butyl-2-(4-ethynylphenyl)-1,3-oxathiane

Participants

Reaction Steps

A solution of 3,3-dimethyl-2-mercaptomethylbutan-1-ol (1.46 g), 4-ethynylbenzaldehyde (1.30 g) (W.B. Austin et al. J. Org. Chem., 1981, 46. 2280) and para-toluenesulphonic acid (10 mg) in benzene (50 ml) was heated to reflux overnight under Dean and Stark conditions. The resulting solution was evaporated under reduced pressure and the residue was purified on silica. Elution with 4:1 hexane: dichloromethane gave 5-t-butyl-2-(4-ethynylphenyl)-1,3-oxathiane as a mixture of isomers.

Provenance & Evidence