Hydrochloric Acid → 3-Hydroxy-2-(p-methoxyphenyl)-5-trifluoromethylbenzo[b]thiophene

HRID 978085ノート

反応式

HRID 978085 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:26]=[CH:25][C:8]([CH2:9][S:10][C:11]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:12]=2[C:13]([O:15]C)=O)=[CH:7][CH:6]=1.O.Cl>CN(C)C=O>[OH:15][C:13]1[C:12]2[CH:17]=[C:18]([C:21]([F:22])([F:24])[F:23])[CH:19]=[CH:20][C:11]=2[S:10][C:9]=1[C:8]1[CH:25]=[CH:26][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 20205034Methyl 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoate

生成物 1

HCID 202050203-Hydroxy-2-(p-methoxyphenyl)-5-trifluoromethylbenzo[b]thiophene

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
75 °C

実験手順

To a mixture of sodium hydride (50% dispersion in mineral oil) (134 mg, 2.79 mmol) in N,N-dimethylformamide (3 ml) at 75° C. under a nitrogen atmosphere was added dropwise with stirring a solution of methyl 2-(p-methoxybenzylthio)-5-trifluoromethylbenzoate (500 mg, 1.40 mmol) in N,N-dimethylformamide (10 ml). After stirring 30 minutes at 75° C., the mixture was poured into water (50 ml), the mixture brought to pH5 with 2N hydrochloric acid, the product extracted with diethyl ether, the combined extracts washed with water, dried (sodium sulfate), and evaporated. The residue was chromatographed on a column of silica gel (Merck 7734, packed as a slurry in 25:1 hexane-ether). Elution with 25:1 hexane-ether containing 1% acetic acid afforded the desired product as a white solid upon evaporation of the appropriate fractions; yield 385 mg (85%); m/z 324 (M+.).

後処理

  1. additionwas added dropwise
  2. extractionthe product extracted with diethyl ether
  3. washthe combined extracts washed with water
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was chromatographed on a column of silica gel (Merck 7734
  7. washElution with 25:1 hexane-ether containing 1% acetic acid

出典と根拠

ORDレコード
ord-3feef361eedd4a3a9a00a5a6d88a2783
出典データセット
uspto-grants-1987_05
特許番号
US04663344

反応ノート

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