2-Methoxy-1-phenylethanone → Ethyl 2-dimethylamino-5-methoxy-6-oxo-6-phenyl-2,4-hexadienoate

HRID 1074051

Reaktionsgleichung

Reaktionsgleichung von HRID 1074051
[C:1]1([C:7](=[O:22])[C:8](SC)=[CH:9][CH:10]=[C:11]([N:17]([CH3:19])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.CN(C)C([C:36](OCC)=[O:37])=CC=[N+](C)C.CC[O-].[Na+].COCC(C1C=CC=CC=1)=O>C(O)C>[CH3:18][N:17]([CH3:19])[C:11](=[CH:10][CH:9]=[C:8]([O:37][CH3:36])[C:7](=[O:22])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

6

Edukt 4

HCID 776982-Methoxy-1-phenylethanoneHCID 2723922Sodium ethoxideHCID 44325574Ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino2,4-hexadienoateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Produkt 1

HCID 53661101Ethyl 2-dimethylamino-5-methoxy-6-oxo-6-phenyl-2,4-hexadienoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The procedure is as in Example 4 for the preparation of ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino-2,4-hexadienoate, starting with N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (11.4 g), a 2M ethanolic solution of sodium ethylate (20 cc) and α-methoxyacetophenone (6 g) in ethanol (50 cc). After purification by chromatography on a silica column with a mixture of dicholoromethane and ethyl acetate (50:50 by volume) as eluent, ethyl 2-dimethylamino-5-methoxy-6-oxo-6-phenyl-2,4-hexadienoate (8.1 g) is obtained, 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 dicholoromethane and ethyl acetate (50:50 by volume) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-f3742059cd16495e9938ee0e06a6d8a8
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971979

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