(Trifluoromethyl)trimethylsilane → 2,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol

HRID 1620836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620836
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH:8]=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:14][C:15]([Si](C)(C)C)([F:17])[F:16]>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:14][C:15]([F:17])([F:16])[CH:8]([C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[OH:9]

Komponenten

5

Edukt 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 104196252-(1H-imidazol-1-yl)benzaldehyde

Produkt 1

HCID 667427962,2,2-Trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724141Tetrabutylammonium FluorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2-imidazol-1-yl-benzaldehyde (0.344 g, 2 mmol) in THF (8 ml) was added trifluoromethyltrimethyl silane (0.341 g, 2.4 mmol). The reaction mixture was cooled to 0-5° C. (ice water bath) and tetra-n-butyl ammonium fluoride (0.035 ml, 0.035 mmol, 1M in THF) was added. The ice bath was removed, and the mixture was stirred at room temperature for 6 hours. 2N HCl (5 ml) was added, and the reaction mixture was further stirred for 3 hours at room temperature. Solvent was removed on the rotavap under reduced pressure. Crude residue was dissolved in DCM (30 ml), washed with water (20 ml), brine (20 ml) and dried with sodium sulfate. The solvent was removed to give crude 2,2,2-trifluoro-1-(2-imidazol-1-yl-phenyl)-ethanol (0.45 g, 93%), which was directly used in the next step.

Aufarbeitung

  1. additionwas added
  2. customThe ice bath was removed
  3. addition2N HCl (5 ml) was added
  4. stirringthe reaction mixture was further stirred for 3 hours at room temperature
  5. customSolvent was removed on the rotavap under reduced pressure
  6. dissolutionCrude residue was dissolved in DCM (30 ml)
  7. washwashed with water (20 ml), brine (20 ml)
  8. dry with materialdried with sodium sulfate
  9. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-b2751d446298487e88058036b2eb5fd8
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772482B2

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