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

HRID 705795Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=[N:3]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of methyl ((E)-Methyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate (18 g, 108 mmol) in ethanol (300 ml) was added Pd/C (4 g, 37.6 mmol) at room temperature. The reaction mixture was stirred at 40° C. for 12 h under hydrogen. The reaction mixture was cooled to room temperature, then the solid was removed by filtration. The filtrate was concentrated in vacuo to give the title compound as colorless oil (17.8 g, 80% yield). LCMS: rt=1.27 min, [M+H+]=169

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solid was removed by filtration
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-947543c1915b4dbba49ab722cdfaa869
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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