Thiophenol → 2-[1-(2-phenylthioethyl)cyclopropyloxy]tetrahydro-4H-pyran

Participants

Reaction Steps

2-[1-(2-p-Toluenesulphonyloxyethyl)cyclopropyloxy]tetrahydro-4H-pyran (Compound 4) (1.30 g) was dissolved in a premixed, stirred solution of potassium tert-butoxide (0.45 g) and thiophenol (0.50 g) in N,N-dimethylformamide (10 ml) at room temperature. After a few minutes a precipitate started forming, and after 30 minutes the mixture was partitioned between ether (50 ml) and water. The organic layer was washed consecutively with 2N sodium hydroxide solution, water, and brine. Drying and concentration in vacuo gave a residue which was purified by chromatography (50 g silica gel; 10% ether in petroleum ether as eluant) to give 2-[1-(2-phenylthioethyl)cyclopropyloxy]tetrahydro-4H-pyran. Distillation of a portion gave an analytical sample, b.p. 121°-122° C./0.1 mmHg. (Found: C, 69.07; H, 8.01; S, 11.31. C16H22O2S requires C, 69.03; H, 7.97; S, 11.52%).

Provenance & Evidence