Sodium ethoxide → Diethyl 2-dimethylamino-5-(2,4,6-trimethylbenzylthio)-2,4-hexadienedioate

HRID 1074094Notes

Reaction equation

HRID 1074094 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]=[C:60]([CH3:62])[CH:59]=[C:58]([CH3:63])[C:49]=1[CH2:50][S:51][CH2:52][C:53]([O:55][CH2:56][CH3:57])=[O:54]>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:52]([S:51][CH2:50][C:49]1[C:58]([CH3:63])=[CH:59][C:60]([CH3:62])=[CH:61][C:48]=1[CH3:47])[C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 13245053Ethyl (2,4,6-trimethylbenzylthio)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 53868150Diethyl 2-dimethylamino-5-(2,4,6-trimethylbenzylthio)-2,4-hexadienedioateYield 45.5%

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 (10 g), a 2M ethanolic solution of sodium ethylate (21 cc) and ethyl (2,4,6-trimethylbenzylthio)acetate (8.8 g) in ethanol (80 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent, diethyl 2-dimethylamino-5-(2,4,6-trimethylbenzylthio)-2,4-hexadienedioate (6.44 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 (70:30 by volume) as eluent

Sources & evidence

ORD record
ord-32f952ac910341e1ac2a5bec02493caa
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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