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

HRID 978085Notes

Reaction equation

[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

Participants

Conditions

Temperature: 75 °C

Procedure

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+.).

Workup

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

Sources & evidence

ORD record: ord-3feef361eedd4a3a9a00a5a6d88a2783
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04663344

Reaction notes

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