Water → 5-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

HRID 589280ノート

反応式

HRID 589280 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([C:10]([O:12]C)=[O:11])=[CH:9][C:5]=2[CH:4]=1.O.[OH-].[Li+].O>CO>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[S:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:5]=2[CH:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 14779565-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 27830435-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid収率 98.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

A mixture of 300 mg of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, 66 mg of lithium hydroxide monohydrate, 2 ml of water and 6 ml of methanol was stirred at 75° C. for 1 hour. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added water, and then washed with tert-butyl methyl ether 3 times. To the aqueous layer was added concentrated hydrochloric acid, and then extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 280 mg of 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid (the present compound 1).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added water
  4. washwashed with tert-butyl methyl ether 3 times
  5. additionTo the aqueous layer was added concentrated hydrochloric acid
  6. extractionextracted with tert-butyl methyl ether 3 times
  7. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b20b741971b347bda8f24b5ccfe5d496
出典データセット
uspto-grants-2016_01
特許番号
US09232792B2

反応ノート

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