Sodium ethoxide → Diethyl 2-dimethylamino-5-(2-methylbenzylthio)-2,4-hexadienedioate

HRID 477354

Reaktionsgleichung

Reaktionsgleichung von HRID 477354
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.CC[O-].[Na+].[CH3:47][C:48]1[CH:61]=[CH:60][CH:59]=[CH:58][C:49]=1[CH2:50][S:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54]>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:52]([S:51][CH2:50][C:49]1[CH:58]=[CH:59][CH:60]=[CH:61][C:48]=1[CH3:47])[C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Komponenten

6

Edukt 4

HCID 2723922Sodium ethoxideHCID 13245059Ethyl (2-methylbenzylthio)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Produkt 1

HCID 53720386Diethyl 2-dimethylamino-5-(2-methylbenzylthio)-2,4-hexadienedioateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

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 (10 g), a 2M ethanolic solution of sodium ethylate (21 cc) and ethyl (2-methylbenzylthio)acetate (7.9 g) in ethanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent, diethyl 2-dimethylamino-5-(2-methylbenzylthio)-2,4-hexadienedioate (9.5 g) is obtained in the form of a yellow oil, and is used in the crude state in the subsequent syntheses.

Aufarbeitung

  1. customAfter purification by chromatography on a silica column
  2. additionwith a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-e6a5bd963247488d9dd60f39fd7d5c11
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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