Allyl bromide → Methyl 2-(allyloxy)propanoate

Temperature

0 °C

(±)-Methyl-2-hydroxypropanoate (7.6 g, 74 mmol) was dissolved in tetrahydrofuran (100 mL), cooled to 0° C. and treated with sodium hydride (3.6 g, 60% dispersion, 89 mmol, 1.2 equiv) portionwise over 45 minutes. The mixture was warmed to ambient temperature, stirred for 30 minutes, and then cooled to 0° C. Allyl bromide (8.4 mL, 96 mmol, 1.3 equiv) was added, the mixture was warmed to ambient temperature and stirred for an additional 14 hours. Sodium bicarbonate (10 mL, aqueous saturated) was added slowly and the mixture was stirred for 30 minutes before being poured into water (500 mL). The aqueous layer was extracted with ethyl acetate (2×300 mL) and the combined organic extracts were washed once with brine, dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

1. temperatureThe mixture was warmed to ambient temperature
2. temperaturecooled to 0° C
3. temperaturethe mixture was warmed to ambient temperature
4. stirringstirred for an additional 14 hours
5. stirringthe mixture was stirred for 30 minutes
6. extractionThe aqueous layer was extracted with ethyl acetate (2×300 mL)
7. washthe combined organic extracts were washed once with brine
8. dry with materialdried with sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-d272c18bd25f4b909d33c8121a6e222e

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486946B2