Isopropanol → Isopropyl 2-cyanoethyl(ethyl)phosphinate
Reaction equation
[CH:1]([O:4][P:5]([CH2:7][CH3:8])[OH:6])([CH3:3])[CH3:2].[C:9](#[N:12])[CH:10]=[CH2:11].C(O)(C)C.[Na]>>[C:9]([CH2:10][CH2:11][P:5]([CH2:7][CH3:8])(=[O:6])[O:4][CH:1]([CH3:3])[CH3:2])#[N:12]Participants
Procedure
To a solution of 262 g of ethyldichlorophosphine in 1200 ml of diethylether is added with stirring and cooling with ice at 5-10° a solution of 370 ml of isopropanol and 280 ml of triethylamine in 400 ml of diethylether. The reaction is exothermic. After stirring for 12 hours at 20° the white precipitate is filtered off and the filtrate is fractionally distilled. There is obtained ethylphosphonous acid-isopropylester as a colorless liquid, b.p. 80-85°/26 kPa. To 34 g of ethylphosphonous acid-isopropylester and 16.45 ml of acrylonitrile is added with stirring 40 ml of isopropanol containing 0.25 mol of sodium isopropylate. The reaction is exothermic. After 1 hour stirring at 20° the mixture is fractionated. There is obtained isopropyl 2-cyanoethyl(ethyl)phosphinate as a colorless oil, b.p. 102-104°/10 Pa.
Sources & evidence
- ORD record
- ord-51b4beb4b69543b693465a0eb18f544b
- Source dataset
- uspto-grants-1991_05
- Patent number
- US05013863
Reaction notes
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