Ethyl Acetate → (4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

HRID 456219

Reaktionsgleichung

Reaktionsgleichung von HRID 456219
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[NH:15][C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[Br:32][C:33]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:34]=1[CH2:35]Br.CCOC(C)=O>C1COCC1.O>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:35][C:34]3[CH:37]=[C:38]([C:41]([F:42])([F:44])[F:43])[CH:39]=[CH:40][C:33]=3[Br:32])[C@H:14]2[CH3:19])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 27562491-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzeneHCID 23583229(4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-oneHCID 45051731Sodium hexamethyidisilazane

Produkt 1

HCID 86650342(4S,5R)-5-(3,5-Bis-trifluoromethyl-phenyl)-3-(2-bromo-5-trifluoromethyl-benzyl)-4-methyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To (4S,5R)-5-(3,5-bis-trifluoromethyl-phenyl)-4-methyl-oxazolidin-2-one (0.246 g, 0.79 mmol) in THF (10 mL) at mom temperature was added sodium hexamethyldisilazane (1M in THF; 1.02 mL, 1.02 mmol), and the reaction was stirred for 15 minutes. 2-Bromo-5-(trifluoromethyl)benzyl bromide (0.250 g, 0.79 mmol) was added, and the reaction was stirred overnight at room temperature. The mixture was worked-up with EtOAc and H2O, and the crude material was purified by silica gel chromatography to give the title compound.

Aufarbeitung

  1. stirringthe reaction was stirred overnight at room temperature
  2. customthe crude material was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8cbfbc09ef2b4a38957e0139f357c329
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497381B2

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