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

HRID 917352

反応式

HRID 917352 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9db6e71ddd914462931406307e242912
出典データセット
uspto-grants-2007_09
特許番号
US07273878B2

関連ノート

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