Ethanol → HCID 178468123, compound

Temperature

0 °C

Under a nitrogen atmosphere, 0.23 g (10 millimoles) of metallic sodium was dissolved in 20 ml of dry ethanol. The solution was cooled to 0° C., and 1.22 g (10 millimoles) of ethyl ethylphosphinate and then 2.40 g (10 millimoles) of ethyl 2-diethoxyphosphinoylpropenoate were added. The mixture was stirred at 0° C. for 1 hour. Cyclohexanecarbaldehyde (1.20 ml; 9.9 millimoles) was added to the mixture, and the reaction was carried out at room temperature for 3 days. Fifty milliliters of a saturated aqueous solution of ammonium chloride was added to the reaction mixture, and the mixture was extracted three times with 50 ml of ethyl acetate each time. The organic layers were washed with 30 ml of a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure liquid chromatography Lobar column (a product of E. Merck & Co.), size C, Lichroprep SI 60, ethyl acetate. The first fraction was evaporated to give 0.33 g (yield 10%) of ethyl (Z)-3-cyclohexyl-2-(ethoxyethylphosphinoyl)methylpropenoate as a colorless oil.

1. waitthe reaction was carried out at room temperature for 3 days
2. extractionthe mixture was extracted three times with 50 ml of ethyl acetate each time
3. washThe organic layers were washed with 30 ml of a saturated aqueous solution of sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by medium-pressure liquid chromatography Lobar column (a product of E
7. customThe first fraction was evaporated

ORD record

ord-e0c9f3a22f0b436f8afde72cd207e226

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04988681