Ethanol → HCID 54557924, compound

HRID 1074074Notes

Reaction equation

HRID 1074074 reaction equation
[C:1]1([C:7](=O)[C:8](SC)=[CH:9][CH:10]=[C:11](N(C)C)[C:12](OCC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.[CH3:28][N:29]([CH3:41])[C:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:32]=[N+](C)C.[CH3:42][CH2:43][O-:44].[Na+].[CH2:46]([OH:48])[CH3:47]>>[CH3:28][N:29]([CH3:41])[C:30](=[CH:31][CH:32]=[C:42]([C:11]1[CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][CH:10]=1)[C:43]([O:48][CH2:46][CH3:47])=[O:44])[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

5

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 44325574Ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino2,4-hexadienoateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 54557924HCID 54557924, compound

Procedure

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 (8 g), a 2M ethanolic solution of sodium ethylate (14 cc) and ethyl 1-(3-biphenylyl)acetate (6.7 g) in ethanol (30 cc). After purification by chromatography on a silica column with dichloromethane as eluent, diethyl 2-dimethylamino-5-(3-biphenylyl)-2,4-hexadienedioate (4.2 g) is obtained in the form of a yellow oil, and is used in the crude state in the subsequent syntheses.

Workup

  1. customAfter purification by chromatography on a silica column with dichloromethane as eluent

Sources & evidence

ORD record
ord-1fd7fc02989448168e5f33a323721e82
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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