Ethyl bromopyruvate → Ethyl 3-bromo-2-(methoxyimino)propanoate

Ethyl bromopyruvate (80% purity), 38.9 g (200 mmol as calculated on an assumption of 100% purity) was dissolved in 100 ml of ethanol. At room temperature, 16.6 g (200 mmol) of methoxyamine hydrochloride was added to the solution, followed by heating under reflux for 2 hours. After reaction had been completed, ethanol was distilled away, and 200 ml of ethyl acetate was added to the residue. The reaction product was washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and an aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. Filtration and subsequent distillation to remove the solvent gave 36.9 g (165 mmol) of ethyl 2-methoxyimino-3-bromopropionate as a light yellow oily matter. The yield was 80%. The product synthesized was subjected to the next reaction without purification.

1. temperatureby heating
2. temperatureunder reflux for 2 hours
3. customAfter reaction
4. distillationethanol was distilled away
5. addition200 ml of ethyl acetate was added to the residue
6. washThe reaction product was washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate
7. dry with materialan aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate
8. filtrationFiltration and subsequent distillation
9. customto remove the solvent

ORD record

ord-110d490f2f9a4fd197058702a4755f9e

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192906B2