Acetylene → 1-Vinyl-4,5,6,7-tetrahydroindole

Participants

Reaction Steps

5 g of cyclohexanone oxime, 1 g of potassium tert.amylate, 125 ml of dimethylsulfoxide and 125 ml of tert-amyl alcohol are heated for a period of 3 hours at a temperature of 120° C in a one-liter rotary autoclave in the presence of a 4-fold excess of acetylene (with respect to the stoichiometric amount thereof). Maximal pressure is 29 atm. The reaction mixture is extracted with diethyl ether and distilled to give 5.6 g (94.9%) of 1-vinyl-4,5,6,7-tetrahydroindole.

Provenance & Evidence