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

1. customThe reaction solution was separated with 30 ml of chloroform and 15 ml of a 4% sodium hydrogencarbonate aqueous solution
2. washThe organic 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 (chloroform)
6. additionThen, the fraction containing the product
7. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=20/1)
8. additionThe combined fraction containing the product
9. customwas subjected to the removal of the solvent under reduced pressure

ORD record

ord-2a1faa763d8e4eeb9b12dae0b20db089

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05481036