Acetic Acid → Ethyl 1-methyl-2-cyanoethyl(diethoxymethyl)phosphinate
Reaction equation
[CH2:1]([O:3][P:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])[O-:5])[CH3:2].[C:13](#[N:17])/[CH:14]=[CH:15]/[CH3:16].[H-].[Na+].C(O)(=O)C>C(O)C>[C:13]([CH2:14][CH:15]([P:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])(=[O:5])[O:3][CH2:1][CH3:2])[CH3:16])#[N:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 23.5 g of ethyl(diethoxymethyl)phosphonite and 6.7 g of crotononitrile in 30 ml of dry ethanol is added to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 ml of ethanol at 0° C. under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature and stirred for 4 hours. 1 ml of glacial acetic acid is added and the mixture concentrated under reduced pressure. The resulting crude product is dissolved in 50 ml of ethyl acetate, washed twice with 25 ml of water, and the organic extract is dried over magnesium sulphate, and the concentrated under reduced pressure. The crude product is distilled under reduced pressure to give ethyl 2-cyano-1-methylethyl(diethoxymethyl)phosphinate, b.p. 116° C./0.01 mbar, 31P=+42.2 and +42.0 ppm (CDCl3).
Workup
- concentrationthe mixture concentrated under reduced pressure
- dissolutionThe resulting crude product is dissolved in 50 ml of ethyl acetate
- washwashed twice with 25 ml of water
- extractionthe organic extract
- dry with materialis dried over magnesium sulphate
- concentrationthe concentrated under reduced pressure
- distillationThe crude product is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-86db6426a8be4e219f4805c50da9cb60
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04772738
Reaction notes
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