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+].[O:47]([C:54]1[CH:55]=[C:56]([CH:65]=[CH:66][CH:67]=1)[CH2:57][S:58][CH2:59][C:60]([O:62][CH2:63][CH3:64])=[O:61])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(O)C>[CH3:29][N:30]([CH3:42])[C:31](=[CH:32][CH:33]=[C:59]([S:58][CH2:57][C:56]1[CH:65]=[CH:66][CH:67]=[C:54]([O:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:55]=1)[C:60]([O:62][CH2:63][CH3:64])=[O:61])[C:37]([O:39][CH2:40][CH3:41])=[O:38]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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 tetraflouroborate (5.7 g), a 2M ethanolic solution of sodium ethylate (10 cc) and ethyl (3-phenoxybenzylthio)acetate (6.1 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-(3-phenoxybenzylthio)-2,4-hexadienedioate (7 g) is obtained in the form of a yellow oil, and is used in the crude state in the subsequent syntheses.
Workup
- customAfter purification by chromatography on a silica column
- additionwith a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluent
Sources & evidence
- ORD record
- ord-91f5c00ab6894e9bb94b49851da2e4fb
- Source dataset
- uspto-grants-1989_12
- Patent number
- US04886835
Linked notes
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