(Trifluoromethyl)trimethylsilane → 6-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

HRID 2096833

Reaktionsgleichung

Reaktionsgleichung von HRID 2096833
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:30])[C:17]([C:19]2[CH:29]=[CH:28][C:22]3[N:23]([CH3:27])[C:24](=[O:26])[O:25][C:21]=3[CH:20]=2)=[O:18])=[C:12]([Cl:31])[CH:11]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:30])[C:17]([C:19]2[CH:29]=[CH:28][C:22]3[N:23]([CH3:27])[C:24](=[O:26])[O:25][C:21]=3[CH:20]=2)([OH:18])[C:2]([F:4])([F:3])[F:1])=[C:12]([Cl:31])[CH:11]=1

Komponenten

5

Edukt 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 666971076-[2-(4-Bromo-2-chloro-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one

Produkt 1

HCID 666970116-[2-(4-Bromo-2-chloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Trifluoromethyltrimethylsilane (2M in THF, 1.48 mL) was added at 0° C. to a solution of 6-[2-(4-bromo-2-chloro-phenyl)-propionyl]-3-methyl-3H-benzooxazol-2-one (531 mg) in THF (15 mL) followed by the addition of tetrabutylammonium fluoride trihydrate (424 mg). Stirring was continued for 48 hours at r.t. The reaction mixture was poured into ice/water and extracted two times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=7:3) to give the title compound as a orange amorphous foam (440 mg, 70%). MS (neg. ion, m/e)=464.0 [(M−H)−].

Aufarbeitung

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica gel, heptane:ethyl acetate=7:3)

Quellen und Nachweise

ORD-Eintrag
ord-cc7d8695385e43a8ab60d5a58d207400
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450313B2

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