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

HRID 1988142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988142
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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 102389871,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(5-phenylbenzoxazol-2-ylmethyl)pentan-2-olAusbeute 76,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fbb8b88ec5db44869591deb10b9338a6
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553966B2

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