Dimethylformamide → 3-Fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide

HRID 225552ノート

反応式

HRID 225552 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:17]([N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])=[O:18].CN([CH:36]=[O:37])C>CCCCCC.C(OCC)C>[F:13][C:14]1[C:15]([CH:36]=[O:37])=[C:16]([CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=1)[C:17]([N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:21])[CH3:22])=[O:18]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 442031433-Fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamideHCID 178418339Butyllithium

生成物 1

HCID 577536553-Fluoro-2-formyl-N,N-diisopropyl-5-trifluoromethyl-benzamide収率 90%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-75 °C

実験手順

A dried 200 ml round-bottomed flask containing 20 ml diethylether was cooled to −75° C. then 22.15 mmol diisopropylamine, 22.15 mmol 1.6M n-butyllithium in hexane, and a solution of 14.77 mmol 3-fluoro-N,N-diisopropyl-5-trifluoromethyl-benzamide in 20 ml diethylether were added sequentially. The mixture was stirred at −75° C. for 2 hours. 2.9 ml DMF was added dropwise. After the reaction was stirred for another hour, the mixture was warmed and stirred at room temperature for 30 minutes. The mixture was quenched with 100 ml 10% citric acid and extracted 3 times with ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light yellow solid (90% yield). MS (m/e): 320.1 (M+H+, 100%)

後処理

  1. stirringAfter the reaction was stirred for another hour
  2. temperaturethe mixture was warmed
  3. stirringstirred at room temperature for 30 minutes
  4. customThe mixture was quenched with 100 ml 10% citric acid
  5. extractionextracted 3 times with ether
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-0f1db3a63b324462a5f48e0996c1747e
出典データセット
uspto-grants-2009_07
特許番号
US07557114B2

反応ノート

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