Water → Methyl methoxy-[2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]acrylate
Reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH:38]=[CH:37][C:36]([O:39][C:40]3[C:45]([C:46](=O)[C:47]([O:49][CH3:50])=[O:48])=[CH:44][CH:43]=[CH:42][N:41]=3)=[N:35]2)=[CH:30][CH:29]=1.O>CN(C)C=O>[CH3:2][O:3][CH:4]=[C:46]([C:45]1[C:40]([O:39][C:36]2[CH:37]=[CH:38][N:34]([C:31]3[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=3)[N:35]=2)=[N:41][CH:42]=[CH:43][CH:44]=1)[C:47]([O:49][CH3:50])=[O:48]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
At room temperature, a mixture of 1.86 g (5.4 mmol) of methoxymethyltriphenylphosphonium chloride and 0.98 g (5.4 mmol) of sodium methoxide solution (30% strength in methanol) in 15 ml of dimethylformamide was stirred for 10 minutes. Subsequently, the reaction mixture was admixed with 1.0 g (2.72 mmol) of methyl [2-(1-(4-chlorophenyl)-3-pyrazolyloxy)pyridin-3-yl]glyoxylate (Example 1a.) dissolved in 5 ml of dimethylformamide. The reaction mixture was stirred at room temperature for 2 hours and then hydrolyzed with 20 ml of water. The aqueous phase was subsequently extracted with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and the solvent was subsequently removed under reduced pressure. 0.6 g (57%) of the title compound was obtained in the form of a yellow solid.
Workup
- stirringThe reaction mixture was stirred at room temperature for 2 hours
- extractionThe aqueous phase was subsequently extracted with methyl tert-butyl ether
- dry with materialThe combined organic phases were dried over sodium sulfate
- customthe solvent was subsequently removed under reduced pressure
Sources & evidence
- ORD record
- ord-ea1786fed8ba4b118b3ff452bad90dfc
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362192B1
Reaction notes
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