Dimethylformamide → HCID 69182537, compound

HRID 917351Notes

Reaction equation

CN(C)C=O.CS([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:16])[F:15])(=O)=O.[S:18]1[C:22]([C:23](O)=[O:24])=[CH:21][C:20]2[CH:26]=[CH:27][CH:28]=[CH:29][C:19]1=2.C(=O)([O-])O.[Na+]>O>[S:18]1[C:22]([C:23]([O:10][CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([F:15])[F:16])=[O:24])=[CH:21][C:20]2[CH:26]=[CH:27][CH:28]=[CH:29][C:19]1=2

Participants

Conditions

Temperature: 100 °C

Procedure

To 5 ml of N,N-dimethylformamide were dissolved 0.40 g (1.8 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate and 0.33 g (1.9 mmol) of benzo[b]thiophene-2-carboxylicacid, followed by the addition of 0.46 g (5.5 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 2 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 concentrating under reduced pressure. The residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:7) to obtain 0.48 g (yield: 93%) of 4,4-difluoro-3-methyl-3-butenyl benzo[b]thiophene-2-carboxylate.

Workup

customThe reaction liquid
extractionextracted with diethyl ether
washThe organic layer was washed with water
dry with materialby drying over anhydrous magnesium sulfate
concentrationconcentrating under reduced pressure
customThe residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:7)

Sources & evidence

ORD record: ord-2a88c3e16cdd4dbf9ec945c3b787e4fa
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273878B2

Reaction notes

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