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

HRID 1074077

Reaction equation

HRID 1074077 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+].[CH:47]([C:50]1[CH:63]=[CH:62][C:53]([CH2:54][S:55][CH2:56][C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:52][CH:51]=1)([CH3:49])[CH3:48]>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:56]([S:55][CH2:54][C:53]1[CH:62]=[CH:63][C:50]([CH:47]([CH3:48])[CH3:49])=[CH:51][CH:52]=1)[C:57]([O:59][CH2:60][CH3:61])=[O:58])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 54329641Ethyl (4-isopropylbenzylthio)acetateHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 54123342Diethyl 2-dimethylamino-5-(4-isopropylbenzylthio)-2,4-hexadienedioateYield 62.2%

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 (4-isopropylbenzylthio)acetate (8.8 g) in ethanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (80:20 by volume) as eluent, diethyl 2-dimethylamino-5-(4-isopropylbenzylthio)-2,4-hexadienedioate (8.8 g) is obtained in the form of an orange-coloured 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 (80:20 by volume) as eluent

Sources & evidence

ORD record
ord-c9742b85e75c4a6cb8887fefae125163
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Linked notes

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