Ethyl bromoacetate → HCID 53640161, compound

To a flask were added 1.5 g diethyl ethylmalonate and 80 ml of tetrahydrofuran and the solution was cooled to 5 C. 0.38 g Sodium hydride were added in small portions and the reaction was stirred for 2 hours at 22 C. After cooling to 5 C, 1.6 g of ethyl bromoacetate were added drop wise and the reaction mixture was allowed to stir at 22 C under nitrogen for 16 hours. After quenching with a few drops of water, the solvent was removed and the crude oil was dissolved in 20 ml tert-butanol and 0.91 g sodium borohydride were added. The mixture was heated to reflux under nitrogen and 1 ml methanol was added drop wise. After stirring for 30 minutes at reflux, the mixture was cooled to 22 C and made acidic with slow addition of 3M hydrochloric acid. Following removal of solvent, the product was purified by silica gel chromatography using pure ethyl acetate resulting in a clear, colorless oil, 0.4 g.

1. temperaturethe solution was cooled to 5 C
2. additionwere added drop wise
3. stirringto stir at 22 C under nitrogen for 16 hours
4. customAfter quenching with a few drops of water
5. customthe solvent was removed
6. dissolutionthe crude oil was dissolved in 20 ml tert-butanol
7. addition0.91 g sodium borohydride were added
8. temperatureThe mixture was heated
9. temperatureto reflux under nitrogen
10. addition1 ml methanol was added drop wise
11. stirringAfter stirring for 30 minutes
12. temperatureat reflux
13. temperaturethe mixture was cooled to 22 C
14. additionmade acidic with slow addition of 3M hydrochloric acid
15. customremoval of solvent
16. customthe product was purified by silica gel chromatography

ORD record

ord-2a40707cd3a94b5685c171ad21b60687

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09011734B2