Hydrochloric Acid → 3-Hydroxy-2-(m-methylphenyl)-5-trifluoromethylbenzo[b]thiophene
Reaction equation
[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]=1Participants
Conditions
- Temperature
- 75 °C
Procedure
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°.
Workup
- additionGas evolution was observed during the 20 minute addition period
- extractionExtraction of the mixture with diethyl ether
- washby washing the combined extracts
- customwith water and evaporation
- customgave a residue that
- customwas chromatographed on a column of silica gel (Merck 7734
- washElution
- customwith 15:1 hexane-ether containing 1% acetic acid and evaporation of the appropriate fractions
Sources & evidence
- ORD record
- ord-f2c1be26f9db41ee8c00ff650ec23a95
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04663344
Reaction notes
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