Hydrochloric Acid → HCID 13359899, compound

To a solution of 4-phenylbutyl phosphonous acid, ethyl ester (0.5 g, 0.0022 mole) in chloroform (15 ml) was added triethylamine (0.34 ml, 0.0024 mole), trimethyl silylchloride (0.31 ml, 0.0024 mole) and methyl acrylate (0.22 ml, 0.0024 mole). The reaction mixture was stirred at room temperature for 4 hours and then stirred at reflux for 23 hours; the mixture was poured into crushed ice (15 gm) containing 10 ml 5% HCl acid. It was shaken in a separatory funnel; a chloroform layer was evaporated, and the aqueous layer extracted once with 20 ml chloroform. The combined organic phase was washed with water and 5% NaHCO3, dried over anhydrous sodium sulphate and the organic solvent removed on a rotavap to produce the title compound as a clear liquid solid (0.6 g). The crude product was purified through column chromatography (1:1 hexane/acetone eluting solvent system) to yield 0.19 g oil.

1. stirringstirred
2. temperatureat reflux for 23 hours
3. additionthe mixture was poured
4. stirringIt was shaken in a separatory funnel
5. customa chloroform layer was evaporated
6. extractionthe aqueous layer extracted once with 20 ml chloroform
7. washThe combined organic phase was washed with water and 5% NaHCO3
8. dry with materialdried over anhydrous sodium sulphate
9. customthe organic solvent removed on a rotavap

ORD record

ord-53bfe6c8aef447eea92a58af9e71dd90

Source dataset

uspto-grants-1986_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04594199