[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid → 2-[4-Methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]ethanol
反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:5][C:6]=1[CH2:7][C:8](O)=[O:9]>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)[S:5][C:6]=1[CH2:7][CH2:8][OH:9]参加物
実験手順
A solution of [4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid (6.01 g, 20 mmol) in tetrahydrofuran (180 ml) was treated at 0° C. with a 1 M solution of BH3*THF in tetrahydrofuran (49.8 ml, 49.8 mmol). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 16 h. Careful quenching with MeOH and ice water, twofold extraction with AcOEt, washing with ice water/brine 1/1, drying over magnesium sulfate, and evaporation of the solvent left a crude product which was refluxed for 30 min in MeOH to liberate quantitatively the free alcohol. The solvent was evaporated in vacuo and the residue was purified by column chromatography (silica gel, dichloromethane/MeOH) to yield 5.68 g (20 mmol, 99%) of the title compound as yellow solid.
後処理
- customThe cooling bath was removed
- customCareful quenching with MeOH and ice water, twofold extraction with AcOEt
- washwashing with ice water/brine 1/1
- dry with materialdrying over magnesium sulfate, and evaporation of the solvent
- waitleft a crude product which
- temperaturewas refluxed for 30 min in MeOH
- customThe solvent was evaporated in vacuo
- customthe residue was purified by column chromatography (silica gel, dichloromethane/MeOH)
出典と根拠
- ORDレコード
- ord-b67eaf779c8842e9b4efb23589e28b78
- 出典データセット
- uspto-grants-2007_06
- 特許番号
- US07235572B2
反応ノート
読み込み中…