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Diisopropylamine → HCID 10287915、化合物

HRID 1070967
ノート
印刷プレビュー

反応式

HRID 1070967 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[O:15][C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]=1[CH3:19].[F:24][C:25]([F:42])([F:41])[C:26](=[O:40])[CH2:27][C:28]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH3:39])([CH3:30])[CH3:29]>C1COCC1>[F:42][C:25]([F:24])([F:41])[C:26]([CH2:13][C:14]1[O:15][C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]=1[CH3:19])([OH:40])[CH2:27][C:28]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH3:39])([CH3:30])[CH3:29]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 27346462,3-DimethylbenzofuranHCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 178418339Butyllithium

生成物 1

HCID 10287915HCID 10287915、化合物収率 47.1%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
3 回

反応条件

温度
-78 °C

実験手順

n-Butyl lithium (0.246 mL, 1.6 M in hexanes) was added to a solution of diisopropyl amine (0.055 mL, 0.45 mmol) in anhydrous THF (5 mL) at 0° C. The reaction mixture was cooled to −78° C. and stirred for 15 minutes. A solution of 2,3-dimethylbenzofuran (48 mg, 0.4 mmol) in 2 mL anhydrous THF was added dropwise to this mixture. After the addition, the reaction mixture was stirred for 15 to 30 minutes. 1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (100 mg, 0.4 mmol) (Example 1) was added as a solution in anhydrous THF (2 mL) in one portion, the cold bath was removed, and the reaction was stirred at room temperature for 12 hours. THF was evaporated under reduced pressure. Water (2 mL) was added to the residue and the mixture was extracted with three 5 mL portions of EtOAc. The extract was dried over magnesium sulfate. After evaporation, the residue was chromatographed on a silica gel column to provide 80 mg of the title compound as an oil.

後処理

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred for 15 to 30 minutes
  3. customthe cold bath was removed
  4. stirringthe reaction was stirred at room temperature for 12 hours
  5. customTHF was evaporated under reduced pressure
  6. additionWater (2 mL) was added to the residue
  7. extractionthe mixture was extracted with three 5 mL portions of EtOAc
  8. dry with materialThe extract was dried over magnesium sulfate
  9. customAfter evaporation
  10. customthe residue was chromatographed on a silica gel column

出典と根拠

ORDレコード
ord-8d1450b233a54a15aa0ceeebf0269fce
出典データセット
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06903215B2

反応ノート

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