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

HRID 1074054

Reaktionsgleichung

Reaktionsgleichung von HRID 1074054
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+].[C:47]1([C:53]2[CH:66]=[CH:65][C:56]([CH2:57][S:58][CH2:59][C:60]([O:62][CH2:63][CH3:64])=[O:61])=[CH:55][CH:54]=2)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:59]([S:58][CH2:57][C:56]1[CH:55]=[CH:54][C:53]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:66][CH:65]=1)[C:60]([O:62][CH2:63][CH3:64])=[O:61])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Komponenten

6

Edukt 4

HCID 2723922Sodium ethoxideHCID 54328963Ethyl (4-phenylbenzylthio)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Produkt 1

HCID 53850243Diethyl 2-dimethylamino-5-(4-phenylbenzylthio)-2,4-hexadienedioateAusbeute 68,6 %

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 (5.7 g), a 2M ethanolic solution of sodium ethylate (10 cc) and ethyl (4-phenylbenzylthio)acetate (5.7 g) in ethanol (50 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-(4-phenylbenzylthio)-2,4-hexadienedioate (6 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-32c0a27da84142dcbaf8f6d4af05ba51
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971979

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