p-Toluenesulfonic acid → 1-Bromo-2-(tetrahydropyran-2-yl)oxypropane

5.0 ml of 1-bromo-2-propanol was dissolved in 40 ml of dry dichloromethane, and 7.6 ml of 2,3-dihydropyran and 237 mg of dry p-toluenesulfonic acid were added thereto. The mixture was reacted at room temperature for 5 hours and then diluted by an addition of 250 ml of chloroform. The mixture was washed sequentially with a 4% sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution. Then, the chloroform layer was dried over anhydrous magnesium sulfate. After filtering the inorganic salt off, the filtrate was concentrated under reduced pressure to obtain a brown syrup. This syrup was purified by silica gel flash column chromatography (130 g of Wacogel C-300 and eluted with hexane/ethyl acetate (15/1). The eluate containing the desired product was collected and concentrated under reduced pressure to obtain 11.3 g of 1-bromo-2-(tetrahydropyran-2-yl)oxypropane as a colorless transparent volatile syrup.

1. customThe mixture was reacted at room temperature for 5 hours
2. washThe mixture was washed sequentially with a 4% sodium hydrogencarbonate aqueous solution
3. dry with materialThen, the chloroform layer was dried over anhydrous magnesium sulfate
4. filtrationAfter filtering the inorganic salt off, the filtrate
5. concentrationwas concentrated under reduced pressure
6. customto obtain a brown syrup
7. customThis syrup was purified by silica gel flash column chromatography (130 g of Wacogel
8. washand eluted with hexane/ethyl acetate (15/1)
9. additionThe eluate containing the desired product
10. customwas collected
11. concentrationconcentrated under reduced pressure

ORD record

ord-3e53f856850847eb99c30f8f89078de6

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04851387