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

HRID 477331

Reaction equation

HRID 477331 reaction equation
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+].[CH3:47][C:48]1[CH:61]=[CH:60][C:51]([CH2:52][S:53][CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])=[CH:50][CH:49]=1>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:54]([S:53][CH2:52][C:51]1[CH:60]=[CH:61][C:48]([CH3:47])=[CH:49][CH:50]=1)[C:55]([O:57][CH2:58][CH3:59])=[O:56])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 4107274Ethyl (4-methylbenzylthio)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 53847987Diethyl 2-dimethylamino-5-(4-methylbenzylthio)-2,4-hexadienedioateYield 66.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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-methylbenzylthio)acetate (4.5 g) in ethanol (50 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent, diethyl 2-dimethylamino-5-(4-methylbenzylthio)-2,4-hexadienedioate (5 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
  2. additionwith a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent

Sources & evidence

ORD record
ord-12abb86c430a49e490d5e491c3c8d3c4
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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