Dimethylformamide → 6,6-Difluoro-5-methyl-5-hexenyl benzo[b]thiophene-2-carboxylate

HRID 917352

반응식

HRID 917352 반응식
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.[S:20]1[C:24]([C:25](O)=[O:26])=[CH:23][C:22]2[CH:28]=[CH:29][CH:30]=[CH:31][C:21]1=2.C(=O)([O-])O.[Na+]>O>[S:20]1[C:24]([C:25]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:17])[F:18])=[O:26])=[CH:23][C:22]2[CH:28]=[CH:29][CH:30]=[CH:31][C:21]1=2

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 230203716,6-Difluoro-5-methyl-5-hexenyl methanesulfonate

생성물 1

HCID 691816906,6-Difluoro-5-methyl-5-hexenyl benzo[b]thiophene-2-carboxylate수율 81%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

To 40 ml of N,N-dimethylformamide were dissolved 5.00 g (22 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 4.30 g (24 mmol) of benzo[b]thiophene-2-carboxylicacid, followed by the addition of 6.00 g (71 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 5.50 g (yield: 81%) of 6,6-difluoro-5-methyl-5-hexenyl benzo[b]thiophene-2-carboxylate.

후처리

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

출처 및 근거

ORD 기록
ord-9db6e71ddd914462931406307e242912
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273878B2

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