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

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%).

1. concentrationThe mixture was concentrated in vacuo
2. dissolutionthe residue dissolved in THF (100 ml)
3. stirringThe mixture was stirred at room temperature for 18 hours
4. concentrationconcentrated in vacuo
5. dissolutionThe residue was dissolved in dichloromethane (200 ml)
6. washwashed with water (50 ml) and brine (50 ml)
7. customThe organic layer was separated
8. dry with materialdried over magnesium sulphate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurification by flash column chromatography on silica eluting with 25% diethyl ether in hexane

ORD record

ord-710967480ea74dd383ea9ca4ee6a259f

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06566384B1