Benzyl Bromide → 2-((Benzyloxy)methyl)tetrahydro-2H-pyran

Temperature

0 °C

At 0° C., a solution of 25.0 g (215 mmol) of tetrahydro-2H-pyran-2-ylmethanol (racemate) in 500 ml of THF was slowly added dropwise to a suspension of 9.47 g (237 mmol, 60% in mineral oil) of sodium hydride in 500 ml of THF, and after the addition had ended, the mixture was stirred at 0° C. for another 30 min 25.7 ml (215 mmol) of benzyl bromide were then added, and the mixture was stirred at 0° C. for another 30 min and at room temperature for another 1 h. The reaction was terminated by addition of 200 ml of saturated aqueous ammonium chloride solution, and the phases were separated. The aqueous phase was extracted twice with 200 ml of methyl tert-butyl ether. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (ethyl acetate/cyclohexane gradient, 340 g silica cartridge, flow rate 100 ml/min), giving the title compound. Yield: 41.9 g (94% of theory)

1. additionafter the addition
2. additionwere then added
3. customThe reaction was terminated by addition of 200 ml of saturated aqueous ammonium chloride solution
4. customthe phases were separated
5. extractionThe aqueous phase was extracted twice with 200 ml of methyl tert-butyl ether
6. dry with materialThe combined organic phases were dried over magnesium sulphate
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customThe crude product was purified by column chromatography (ethyl acetate/cyclohexane gradient, 340 g silica cartridge, flow rate 100 ml/min)

ORD record

ord-6423bf4f950e44b3a1735176db6b8d4b

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434690B2