Dimethyl Sulfoxide → 1-Vinyl-4,5,6,7-tetrahydroindole

Participants

Reaction Steps

5 g of cyclohexanone oxime, 2.5 g of sodium hydroxide, 100 ml of dimethylsulfoxide and 5 ml of pyridine are heated for 3 hours at a temperature of 90° C in a one-liter rotary autoclave in the presence of a 5-fold excess of acetylene (with respect to the stoichiometric amount thereof). Maximal pressure is 27 atm. The reaction mixture is extracted with diethyl ether and distilled to give 5.3 g (90%) of 1-vinyl-4,5,6,7-tetrahydroindole.

Provenance & Evidence