3,4-dihydro-2H-pyran → HCID 18533049, compound

Participants

Reaction Steps

To a solution of 4-hydroxythiophenol (10 g, 79 mmol) and p-toluenesulphonic acid (100 mg) in dichloromethane (100 ml) was added dihydropyran (16.7 g, 19.8 mmol) and the mixture stirred at room temperature for 18 hours. The mixture was concentrated in vacuo and the residue dissolved in THF (100 ml) and 0.5 M sulphuric acid (20 ml). The mixture was stirred at room temperature for 18 hours and concentrated in vacuo. The residue was dissolved in dichloromethane (200 ml) and washed with water (50 ml) and brine (50 ml). The organic layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo. Purification by flash column chromatography on silica eluting with 25% diethyl ether in hexane afforded the title compound as a white solid (11.5 g, 66%).

Provenance & Evidence