Ethyl (phenethylthio)acetate → Ethyl 5-dimethylamino-5-phenyl-2-phenethylthio-2,4-pentadienoate

HRID 477369

Reaktionsgleichung

Reaktionsgleichung von HRID 477369
[CH3:1][N:2]([CH3:24])[C:3]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:4][CH:5]=[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[S:8].F[B-](F)(F)F.CN(C)[C:32](C1C=CC=CC=1)=[CH:33]C=[N+](C)C.CC[O-].[Na+].C(SCC(OCC)=O)CC1C=CC=CC=1>C(O)C>[CH3:24][N:2]([CH3:1])[C:3]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[CH:4][CH:5]=[C:6]([CH2:12][CH2:17][C:16]1[CH:15]=[CH:14][CH:13]=[CH:33][CH:32]=1)[C:7]([O:9][CH2:10][CH3:11])=[S:8]

Komponenten

6

Edukt 4

HCID 304016Ethyl (phenethylthio)acetateHCID 2723922Sodium ethoxideHCID 75556698N-(3-dimethylamino-3-phenylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743587Ethyl 5-dimethylamino-5-phenyl-2-phenylthio-2,4-pentadienoate

Produkt 1

HCID 86743602Ethyl 5-dimethylamino-5-phenyl-2-phenethylthio-2,4-pentadienoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The procedure is as in Example 24 for the preparation of ethyl 5-dimethylamino-5-phenyl-2-phenylthio-2,4-pentadienoate, starting with N-(3-dimethylamino-3-phenylpropenylidene)-N-methylmethanaminium tetrafluoroborate (5.8 g), a 2M ethanolic solution of sodium ethylate (10 cc) and ethyl (phenethylthio)acetate (4.5 g) in ethanol (50 cc). After purification by chromatography on a silica column with dichloromethane as eluent, ethyl 5-dimethylamino-5-phenyl-2-phenethylthio-2,4-pentadienoate (4.5 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 with dichloromethane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-2ff60aa7020648b68f550d40016ce591
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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