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

HRID 477346Notes

Reaction equation

HRID 477346 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]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[CH:50]=[CH:49][C:48]=1[S:57][CH2:58][C:59]([O:61][CH2:62][CH3:63])=[O:60]>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:58]([S:57][C:48]1[CH:49]=[CH:50][C:51]2[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:47]=1)[C:59]([O:61][CH2:62][CH3:63])=[O:60])[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 11253633HCID 11253633, compoundHCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborateHCID 86743580Diethyl 2-dimethylamino-5-phenylthio-2,4-hexadienedioate

Product 1

HCID 53675589Diethyl 2-dimethylamino-5-(2-naphthylthio)-2,4-hexadienedioateYield 82.3%

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-naphthylthio)acetate (12.9 g) in ethanol (100 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-(2-naphthylthio)-2,4-hexadienedioate (11.5 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-8ab4c7dbad554527aa7fee8bb02678d3
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Reaction notes

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