Dimethylformamide → 4,4-difluoro-3-methyl-3-butenyl 3-methyl-1-phenyl-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To 5 ml of N,N-dimethylformamide were dissolved 0.57 g (2.8 mmol) of 3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid, obtained in accordance with a method described in J. Chem. Soc., page 2736 (1961), and 0.58 g (2.9 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate, followed by the addition of 0.48 g (5.7 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:6) to obtain 0.66 g (yield: 76%) of 4,4-difluoro-3-methyl-3-butenyl 3-methyl-1-phenyl-1H-pyrazole-4-carboxylate.

Provenance & Evidence