Dimethylformamide → 5-tert-Butyl-2-(4-ethynylphenyl)-1,3-dithiane

Participants

Reaction Steps

A mixture of 4-ethynylbenzaldehyde (131 mg., 1.00 mmol.), 2-t-butylpropane-1,3-dithiol (206 mg., 1.25 mmole) (E. L. Eliel and R. O. Hutchins (J. Amer. Chem. Soc. 1969, 91, 2703)) and the adduct of N,N-dimethylformamide and dimethyl sulphate (300 mg., 1.50 mmole) diluted with methylene chloride (2.0 ml.) was maintained at 23° for 48 hours. After cooling to 0°, triethylamine (0.2 ml) was added, and the solution was washed with water (3×2 ml.) which was again extracted with methylene chloride. The combined organic layers were dried (anhydrous magnesium sulphate) and evaporated to give a residue (320 mg.) which was recrystallized from hexane (2.5 ml.) to give 2-(4-ethynylphenyl)-5-t-butyl-1,3-dithiane, m.p. 149°, (120 mg , 43%)

Provenance & Evidence