Acetic Acid → Ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate

HRID 542301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542301
[CH2:1]([O:3][P:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])[O-:5])[CH3:2].[Cl:13][C:14]1[CH:23]=[CH:22][C:17]([CH:18]=[CH:19][C:20]#[N:21])=[CH:16][CH:15]=1.[H-].[Na+].C(O)(=O)C>C(O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH:18]([P:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])(=[O:5])[O:3][CH2:1][CH3:2])[CH2:19][C:20]#[N:21])=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 342433-(4-Chlorophenyl)prop-2-enenitrileHCID 85631043Ethyl(diethoxymethyl)phophonite

Produkt 1

HCID 14362807Ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

The starting material may be prepared as follows: A solution of 25.8 g of ethyl(diethoxymethyl)phosphonite and 18.0 g of 4-chlorocinnamonitrile in 100 ml of 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 is 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 then concentrated under reduced pressure. The crude product is distilled under reduced pressure to give ethyl 1-(4-chlorophenyl)-2-cyanoethyl(diethoxymethyl)phosphinate, b.p. 180°-200° C./0.02 mbar, 31P=+37.9 and +37.8 ppm (CDCl3).

Aufarbeitung

  1. customThe starting material may be prepared
  2. concentrationthe mixture is concentrated under reduced pressure
  3. dissolutionThe resulting crude product is dissolved in 50 ml of ethyl acetate
  4. washwashed twice with 25 ml of water
  5. extractionthe organic extract
  6. dry with materialis dried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. distillationThe crude product is distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2c53bce63d364e14ae897a2cbb6c1e75
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04656298

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