Toluene → N-(4-Chloro-3-Hydroxymethyl-Phenyl)-3-Trifluoromethyl-Benzamide

HRID 1662809ノート

反応式

HRID 1662809 の反応式
[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]

参加物

5

反応物 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 534011722-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acid

生成物 1

HCID 58901699N-(4-Chloro-3-Hydroxymethyl-Phenyl)-3-Trifluoromethyl-Benzamide収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  1. temperaturethe solution was refluxed under argon for overnight
  2. customThe solution was quenched by minimum amount of methanol and water
  3. customThe organic solvent was removed by reduced pressure
  4. extractionextracted by ethyl acetate (2×50 mL)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customThe organic solvent was removed
  9. customthe crude product was purified by silica gel column with CHCl3 as an eluent

出典と根拠

ORDレコード
ord-c9f6b783b3034309bf1dedf980818231
出典データセット
uspto-grants-2011_10
特許番号
US08030487B2

反応ノート

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