反应详情

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%).

1. customAfter a few minutes a precipitate started forming
2. customafter 30 minutes the mixture was partitioned between ether (50 ml) and water
3. washThe organic layer was washed consecutively with 2N sodium hydroxide solution, water, and brine
4. customDrying
5. concentrationconcentration in vacuo
6. customgave a residue which
7. customwas purified by chromatography (50 g silica gel; 10% ether in petroleum ether as eluant)