Phenylacetonitrile → Ethyl 2-dimethylamino-5-cyano-5-phenyl-2,4-pentadienoate

HRID 477304

Reaktionsgleichung

Reaktionsgleichung von HRID 477304
CN(C)C(=CC=C(C1C=CC=CC=1)C(OCC)=O)C(OCC)=S.F[B-](F)(F)F.[CH3:29][N:30]([CH3:42])[C:31]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:33]=[N+](C)C.[CH2:43]([C:50]#[N:51])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>CC[O-].[Na+]>[CH3:42][N:30]([CH3:29])[C:31](=[CH:32][CH:33]=[C:43]([C:50]#[N:51])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Komponenten

5

Edukt 3

HCID 8794PhenylacetonitrileHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Produkt 1

HCID 54027283Ethyl 2-dimethylamino-5-cyano-5-phenyl-2,4-pentadienoateAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2723922Sodium ethoxideLösungsmittel

Versuchsvorschrift

The procedure is as in Example 2 for the preparation of diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (57.2 g), a 2M ethanolic solution of sodium ethylate (105 cc) and benzyl cyanide (23.4 g). Ethyl 2-dimethylamino-5-cyano-5-phenyl-2,4-pentadienoate (36.1 g), m.p. 67° C., is obtained.

Quellen und Nachweise

ORD-Eintrag
ord-01806bcea28f4f9cb4632d80fa6ae209
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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