Diisopropylamine → 1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(5-phenylbenzoxazol-2-ylmethyl)pentan-2-ol

HRID 2080567ノート

反応式

HRID 2080567 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][C:17]=2[N:18]=1.[F:29][C:30]([F:47])([F:46])[C:31](=[O:45])[CH2:32][C:33]([C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[O:43][CH3:44])([CH3:35])[CH3:34]>C1COCC1>[F:47][C:30]([F:29])([F:46])[C:31]([CH2:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][C:17]=2[N:18]=1)([OH:45])[CH2:32][C:33]([C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[O:43][CH3:44])([CH3:35])[CH3:34]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 112786Benzoxazole, 2-methyl-5-phenyl-HCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneHCID 178418339Butyllithium

生成物 1

HCID 102389871,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(5-phenylbenzoxazol-2-ylmethyl)pentan-2-ol収率 76.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran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. 2-Methyl-5-phenyl benzoxazole (75 mg, 0.4 mmol) dissolved in anhydrous THF (2 mL) was added to this mixture dropwise. 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) 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 150 mg of the title compound as white crystals, m.p. 103° C.-104° C.

後処理

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

出典と根拠

ORDレコード
ord-03666fcd5e5c44e98b05cc266221926d
出典データセット
uspto-grants-2011_04
特許番号
US07932392B2

反応ノート

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