Benzyl Bromide → (R)-5-Benzyloxymethyl-dihydro-furan-2-one

To a solution of (R)-5-hydroxymethyl-dihydro-furan-2-one (5 g, 43.06 mmol) in tetrahydrofuran (130 mL) is added sodium hydride (2.58 g, 60% oil dispersion, 64.59 mmol) and tetrabutylammonium iodide (spatula) and stirred for 30 min. To the mixture is added benzyl bromide (6.18 mL, 51.67 mmol) and refluxed for 3 h. The mixture is cooled and diluted with ethyl acetate (150 mL), washed with a saturated solution of ammonium chloride (150 mL) and brine. The mixture is dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound, 8.87 g (100%), as a pale yellow oil.

1. temperaturerefluxed for 3 h
2. temperatureThe mixture is cooled
3. washwashed with a saturated solution of ammonium chloride (150 mL) and brine
4. dry with materialThe mixture is dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-b1c79f3c05474aeeb8f26acb075fcc5f

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07087626B2