Potassium Hydroxide → (2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acid

Temperature

70 °C

(E)-methyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate (0.24 g, 1.45 mmol) was dissolved in MeOH (10 mL). A 1M solution of KOH (5.8 mL) was added and the mixture was heated at 70° C. overnight. The reaction mixture was then evaporated under reduced pressure and water (10 mL) was added to the residue. This solution was carefully acidified to pH 4 with a 3M aqueous solution of HCl. The carboxylic acid precipitated and was extracted with ethyl acetate. The EtOAc layer was washed with water (2×10 mL) and brine (1×15 mL). It was dried over sodium sulfate, filtered and evaporated under vacuum to give (E)-3-(1-methyl-1H-pyrazol-4-yl)acrylic acid as a white solid (160 mg). ES+(M+H)+153

1. customThe reaction mixture was then evaporated under reduced pressure and water (10 mL)
2. additionwas added to the residue
3. customThe carboxylic acid precipitated
4. extractionwas extracted with ethyl acetate
5. washThe EtOAc layer was washed with water (2×10 mL) and brine (1×15 mL)
6. dry with materialIt was dried over sodium sulfate
7. filtrationfiltered
8. customevaporated under vacuum

ORD record

ord-3665a68fb83a4f2da6c304c861425e85

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957066B2