Dimethylformamide → Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 1776083ノート

反応式

HRID 1776083 の反応式
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:11][C:10]([F:13])([F:12])[C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:15]([C:14]([O:18][CH3:19])=[O:17])[S:16][C:2]=2[CH:9]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

生成物 1

HCID 18526202Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate収率 56.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A mixture of 1.11 g of 2-fluoro-4-(trifluoromethyl)benzaldehyde, 739 mg of methyl thioglycolate, 1.3 g of potassium carbonate and 20 ml of DMF was stirred at 140° C. for 2 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the mixture was extracted with tert-butyl methyl ether three times. The combined organic layers were washed with water and saturated saline, and dried over magnesium sulfate, then, concentrated under reduced pressure, to obtain 848 mg of methyl 6-(trifluoromethyl)benzo[b]thiophene-2carboxylate (present condensed ring compound 2).

後処理

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. extractionthe mixture was extracted with tert-butyl methyl ether three times
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-be41325f571742ba84d855f4424e8a88
出典データセット
uspto-grants-2016_02
特許番号
US09265251B2

反応ノート

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