Dimethylformamide → 6,6-difluoro-5-methyl-5-hexenyl 4-chloro-5-ethyl-2-methyl-2H-pyrazole-3-carboxylate

HRID 917355

Reaction equation

CN(C)C=O.CS([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])(=O)=O.[Cl:20][C:21]1[C:25]([CH2:26][CH3:27])=[N:24][N:23]([CH3:28])[C:22]=1[C:29](O)=[O:30].C(=O)([O-])O.[Na+]>O>[Cl:20][C:21]1[C:25]([CH2:26][CH3:27])=[N:24][N:23]([CH3:28])[C:22]=1[C:29]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])=[O:30]

Participants

Conditions

Temperature: 100 °C

Procedure

To 10 ml of N,N-dimethylformamide were dissolved 0.50 g (2.2 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 0.45 g (2.4 mmol) of 4-chloro-5-ethyl-2-methyl-2H-pyrazole-3-carboxylic acid, followed by the addition of 0.37 g (4.4 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 7 hours. The reaction liquid was then poured in water and extracted with ethyl acetate. 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=1:19) to obtain 0.52 g (yield: 74%) of 6,6-difluoro-5-methyl-5-hexenyl 4-chloro-5-ethyl-2-methyl-2H-pyrazole-3-carboxylate.

Workup

customThe reaction liquid
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:19)

Sources & evidence

ORD record: ord-9bacae5831f746ef887ffa4a56025a9f
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273878B2

Linked notes

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