p-Toluenesulfonic acid → 2-(3-Bromopropoxy)tetrahydro-2H-pyran

0.58 ml of 3-bromo-1-propanol was dissolved in 6 ml of dry dichloromethane, and 1.22 ml of dihydropyran and 10 mg of dry p-toluenesulfonic acid were added thereto. The mixture was stirred at room temperature overnight, and the mixture was partitioned with 30 ml of chloroform and 15 ml of a 4% sodium hydrogencarbonate aqueous solution. The organic solvent layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was separated by silica gel column chromatography (10 g of Kieselgel 60) by using chloroform. Then, the fraction containing the product was purified by silica gel column chromatography (10 g of Kieselgel 60) by using a mixture of n-hexane/ethyl acetate (20/1). The fractions containing the product were put together, and the solvent was distilled off under reduced pressure to obtain 1.44 g of 3-bromo-1-(2-tetrahydropyranyloxy)propane as a colorless oily substance.

1. customthe mixture was partitioned with 30 ml of chloroform and 15 ml of a 4% sodium hydrogencarbonate aqueous solution
2. washThe organic solvent layer was washed with water
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationThe solvent was distilled off under reduced pressure
5. customThe residue was separated by silica gel column chromatography (10 g of Kieselgel 60)
6. additionThen, the fraction containing the product
7. customwas purified by silica gel column chromatography (10 g of Kieselgel 60)
8. additiona mixture of n-hexane/ethyl acetate (20/1)
9. additionThe fractions containing the product
10. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-781ab957363b4e60a424d5129416aadb

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04851387