Sodium ethoxide → Diethyl 2-dimethylamino-5-(3-benzoylphenyl)-2,4-hexadienedioate

HRID 477351Notes

Reaction equation

HRID 477351 reaction equation
C1(C(=O)C(SC)=CC=C(N(C)C)C(OCC)=O)C=CC=CC=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.CC[O-].[Na+].[C:46]([C:54]1[CH:55]=[C:56]([CH2:60][C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH:57]=[CH:58][CH:59]=1)(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(O)C>[CH3:28][N:29]([CH3:41])[C:30](=[CH:31][CH:32]=[C:60]([C:56]1[CH:57]=[CH:58][CH:59]=[C:54]([C:46](=[O:53])[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[CH:55]=1)[C:61]([O:63][CH2:64][CH3:65])=[O:62])[C:36]([O:38][CH2:39][CH3:40])=[O:37]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 44325574Ethyl 6-phenyl-6-oxo-5-methylthio-2-dimethylamino2,4-hexadienoateHCID 53948061Ethyl (3-benzoylphenyl)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 53826129Diethyl 2-dimethylamino-5-(3-benzoylphenyl)-2,4-hexadienedioateYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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 (17.8 g), a 2M ethanolic solution of sodium ethylate (31.3 cc) and ethyl (3-benzoylphenyl)acetate (16.8 g) in ethanol (100 cc). After purification by chromatography on a silica column with dichloromethane as eluent, diethyl 2-dimethylamino-5-(3-benzoylphenyl)-2,4-hexadienedioate (14 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-c67f7ca8bef04f55b2e96b2bdbfab157
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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