C([O-])([O-])=O.[Cs+].[Cs+].[NH:7]1[CH:11]=C(C=O)[CH:9]=[N:8]1.C[C:15](P(OC)(O)=O)([C:17]([O-:19])=[O:18])[CH3:16].[CH3:25]S(C)=O.O1[CH2:34][CH2:33]OCC1>CCOC(C)=O>[CH3:9][N:8]1[CH:34]=[C:33](/[CH:16]=[CH:15]/[C:17]([O:19][CH3:25])=[O:18])[CH:11]=[N:7]1Cs2CO3 (1.304 g, 4 mmol) was added to a solution of 1H-pyrazole-4-carbaldehyde (0.192 g, 2 mmol) in dioxane (8 mL) at room temperature. Trimethylphosphonoacetate (0.364 g, 0.40 mmol) was added to this suspension, followed by DMSO (2 mL). The reaction mixture was heated to 100° C. overnight. It was then diluted with EtOAc (40 mL), and washed with water (40 mL) and brine (20 mL). The organic layer was concentrated under vacuum. The crude was purified by silica gel column chromatography using a 0-100% gradient of EtOAc in hexanes to provide (E)-methyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate (0.278 g). ES+(M+H)+167
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