Sodium hydride → 1-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-3-(trifluoromethyl)-1H-pyrazole

HRID 1025680

Reaktionsgleichung

Reaktionsgleichung von HRID 1025680
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[H-].[Na+].CS(O[CH:17]1[CH2:22][CH2:21][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:19][CH2:18]1)(=O)=O>CN(C=O)C>[Si:24]([O:23][CH:20]1[CH2:19][CH2:18][CH:17]([N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:9])([F:8])[F:1])=[N:4]2)[CH2:22][CH2:21]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 18070343-(Trifluoromethyl)pyrazoleHCID 866346564-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl methanesulfonate

Produkt 1

HCID 595560591-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohexyl)-3-(trifluoromethyl)-1H-pyrazoleAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 3-trifluoromethyl-1H-pyrazole (1.0 g, 7.35 mmol) in DMF (10 mL) cooled in an ice bath was added NaH (0.3 g, 60% in mineral oil). The mixture was stirred for 10 minutes before the mesylate (1.13 g, 3.68 mmol) of step B in DMF (5 mL) was added. Stirring was continued at room temperature for 1 hour and then at 100° C. overnight. After being cooled to room temperature, the solution was poured into ice water and extracted with EtOAc three times. The combined extract was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 5:1 EtOAc/hexanes provided the title compound (0.56 g, 44%) as an oil. MS calculated (M+H)+ 349, found 349.

Aufarbeitung

  1. additionwas added
  2. customat 100° C.
  3. customovernight
  4. extractionextracted with EtOAc three times
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customPurification on silica gel eluting with 5:1 EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c9a0eedcd18a491db7fc1d19240bb1b4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729063B2

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