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

HRID 978088노트

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HRID 978088 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 137877293-Hydroxy-2-(m-methylphenyl)-5-trifluoromethylbenzo[b]thiophene

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
75 °C

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-f2c1be26f9db41ee8c00ff650ec23a95
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04663344

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