Hydrochloric Acid → 3-Hydroxy-2-(m-methylphenyl)-5-trifluoromethylbenzo[b]thiophene

HRID 978088ノート

反応式

HRID 978088 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH2:7][S:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:10]=1[C:11]([O:13]C)=O.O.Cl>CN(C)C=O>[OH:13][C:11]1[C:10]2[CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:18][C:9]=2[S:8][C:7]=1[C:6]1[CH:23]=[CH:24][CH:25]=[C:4]([CH3:3])[CH:5]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 13787728Methyl 2-(m-methylbenzylthio)-5-trifluoromethylbenzoate

生成物 1

HCID 137877293-Hydroxy-2-(m-methylphenyl)-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 slurry of sodium hydride (50% dispersion in mineral oil) (253 mg, 5.27 mmol) in N,N-dimethylformamide (3 ml) at 75° C. under a nitrogen atmosphere was added a solution of methyl 2-(m-methylbenzylthio)-5-trifluoromethylbenzoate (885 mg, 2.60 mmol) in N,N-dimethylformamide (12 ml). Gas evolution was observed during the 20 minute addition period. After stirring an additional 45 minutes at 75° C., water (70 ml) was added, and the aqueous mixture was brought to pH5-6 at room temperature with 2N hydrochloric acid. Extraction of the mixture with diethyl ether followed by washing the combined extracts with water and evaporation gave a residue that was chromatographed on a column of silica gel (Merck 7734, packed as a slurry in 15:1 hexane-ether). Elution with 15:1 hexane-ether containing 1% acetic acid and evaporation of the appropriate fractions afforded the product as a white crystalline solid; yield 450 mg (56%); m/z 308 (M+.); m.p. 124°-126°.

後処理

  1. additionGas evolution was observed during the 20 minute addition period
  2. extractionExtraction of the mixture with diethyl ether
  3. washby washing the combined extracts
  4. customwith water and evaporation
  5. customgave a residue that
  6. customwas chromatographed on a column of silica gel (Merck 7734
  7. washElution
  8. customwith 15:1 hexane-ether containing 1% acetic acid and evaporation of the appropriate fractions

出典と根拠

ORDレコード
ord-f2c1be26f9db41ee8c00ff650ec23a95
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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