Dimethylformamide → HCID 69179458, compound

HRID 917372Notes

Reaction equation

CN(C)C=O.[CH2:6]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=1)[CH2:7][CH2:8][CH3:9].CS(O[CH2:25][CH2:26][C:27]([CH3:31])=[C:28]([F:30])[F:29])(=O)=O.C(=O)([O-])O.[Na+]>O>[CH2:6]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:17][CH2:25][CH2:26][C:27]([CH3:31])=[C:28]([F:30])[F:29])=[O:16])=[CH:13][N:12]=1)[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To 5 ml of N,N-dimethylformamide were dissolved 0.39 g (2.0 mmol) of 6-butoxynicotinic acid, synthesized by a method in accordance with one used in Intermediate Production Example 1, and 0.40 g (2.0 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate, followed by the addition of 0.34 g (4.0 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 (diisopropyl ether:hexane=1:7) to obtain 0.45 g (yield: 75%) of 4,4-difluoro-3-methyl-3-butenyl 6-butoxynicotinate.

Workup

customsynthesized by a method in accordance with one
customThe reaction liquid
extractionextracted with diethyl ether
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 (diisopropyl ether:hexane=1:7)

Sources & evidence

ORD record: ord-47d3cf1e3a0046b59dd9e976ab42940e
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273878B2

Reaction notes

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