Toluene → N-(4-Chloro-3-Hydroxymethyl-Phenyl)-3-Trifluoromethyl-Benzamide
Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:18])=[C:13]([CH:17]=1)[C:14](O)=[O:15])=[O:7].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1COCC1>[Cl:18][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:19]=[CH:20][CH:21]=[C:3]([C:2]([F:23])([F:22])[F:1])[CH:4]=2)=[CH:17][C:13]=1[CH2:14][OH:15]Participants
Procedure
To a solution of intermediate 1 (Example 2) (1.4 g, 4.1 mmol) in anhydrous THF (20 mL) at room temperature under argon, 1.5 M diisobutylaluminum hydride in toluene (DIBAL-H, 9 mL, 13.5 mmol) was added. After the reaction mixture was stirred at room temperature for 1 h, the solution was refluxed under argon for overnight. The solution was quenched by minimum amount of methanol and water. The organic solvent was removed by reduced pressure. The crude was suspended in water (50 mL) and extracted by ethyl acetate (2×50 mL). The organic layers were combined, washed with brine, dried over Na2SO4 and filtered. The organic solvent was removed and the crude product was purified by silica gel column with CHCl3 as an eluent to give the final product as a white solid (700 mg, 52%).
Workup
- temperaturethe solution was refluxed under argon for overnight
- customThe solution was quenched by minimum amount of methanol and water
- customThe organic solvent was removed by reduced pressure
- extractionextracted by ethyl acetate (2×50 mL)
- washwashed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe organic solvent was removed
- customthe crude product was purified by silica gel column with CHCl3 as an eluent
Sources & evidence
- ORD record
- ord-c9f6b783b3034309bf1dedf980818231
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08030487B2
Reaction notes
Loading…