Dimethylformamide → HCID 69179969, compound

HRID 917360Notes

Reaction equation

CN(C)C=O.CS([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:21])=[C:18]([F:20])[F:19])(=O)=O.[S:22]1[C:26]([C:27](O)=[O:28])=[CH:25][C:24]2[CH:30]=[CH:31][CH:32]=[CH:33][C:23]1=2.C(=O)([O-])O.[Na+]>O>[S:22]1[C:26]([C:27]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([CH3:21])=[C:18]([F:19])[F:20])=[O:28])=[CH:25][C:24]2[CH:30]=[CH:31][CH:32]=[CH:33][C:23]1=2

Participants

Conditions

Temperature: 100 °C

Procedure

To 10 ml of N,N-dimethylformamide were dissolved 0.29 g (1.1 mmol) of 8,8-difluoro-7-methyl-7-octenyl methanesulfonate and 0.26 g (1.5 mmol) of benzo[b]thiophene-2-carboxylic acid, followed by the addition of 0.28 g (3.3 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=1:8) to obtain 0.27 g (yield: 71%) of 8,8-difluoro-7-methyl-7-octenyl 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 and concentration under reduced pressure
customThe residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:8)

Sources & evidence

ORD record: ord-3b88855dfd6648ad852e83cd7dae3ac1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273878B2

Reaction notes

Loading…