Dimethyl Sulfoxide → Methyl (2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoate

HRID 1850052Notes

Reaction equation

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]1

Participants

Conditions

Temperature: 100 °C

Procedure

Cs2CO3 (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

Workup

washwashed with water (40 mL) and brine (20 mL)
concentrationThe organic layer was concentrated under vacuum
customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-6ead15fa6db54bcb83861625a6c0174c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957066B2

Reaction notes

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