Triethyl phosphonoacetate → (Diethoxyphosphinyl)acetic acid

Ethyl diethylphosphonoacetate (100 g, 446 mmol) was dissolved in ethanol (275 ml), and after adding dropwise a 2 mol/l aqueous sodium hydroxide solution (275 ml, 550 mmol) while stirring and cooling with ice, it was stirred at room temperature for 1 hour. The reaction solution was then concentrated under a reduced pressure, and the concentrate was made acidic by concentrated hydrochloric acid while cooling with ice. Extractions into ethyl acetate (200 ml×4), chloroform (100 ml×2) and 5% methanol/chloroform (250 ml×2) were then performed. The combined organic layers were then dried over anhydrous sodium sulfate, and after filtering, the filtrate was concentrated under a reduced pressure. 89 g (quantitative) of the title compound was thereby obtained as a colorless, oily substance.

1. temperaturecooling with ice, it
2. stirringwas stirred at room temperature for 1 hour
3. concentrationThe reaction solution was then concentrated under a reduced pressure
4. temperaturewhile cooling with ice
5. extractionExtractions into ethyl acetate (200 ml×4), chloroform (100 ml×2) and 5% methanol/chloroform (250 ml×2)
6. dry with materialThe combined organic layers were then dried over anhydrous sodium sulfate
7. filtrationafter filtering
8. concentrationthe filtrate was concentrated under a reduced pressure

ORD record

ord-0e4f833f581f4c63afdc73b36bd66bc5

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902226B2