Selectfluor → 5-tert-Butyl-4-fluoro-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 1191173

Reaktionsgleichung

Reaktionsgleichung von HRID 1191173
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[O:5])[CH3:2].[B-](F)(F)(F)[F:17].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:10]=1[F:17])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 2724933SelectfluorHCID 2799344ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

Produkt 1

HCID 674133345-tert-Butyl-4-fluoro-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-tert-Butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (210 mg, 1.00 mmol) was added dropwise to a stirred solution of SELECTFLUOR® (531 mg, 1.50 mmol) in anhydrous acetonitrile (4 mL) under an Ar atmosphere. The resulting mixture was then stirred at 80° C. for 12 h, then cooled to room temperature, diluted with EtOAc (2 mL), and filtered. The solvent was removed under reduced pressure and the resulting residue was chromatographed on a 24-g SiO2 pre-packed column eluting with 0:1-1:4 EtOAc/hexanes to yield 5-tert-Butyl-4-fluoro-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester. 1H-NMRH-NMR (400 MHz, CDCl3) δ: 4.37 (q, J=7.2 Hz, 2H), 4.03 (d, J=1.0 Hz, 3H), 1.39 (t, J=7.1 Hz, 3H), 1.34 (s, 9H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting residue was chromatographed on a 24-g SiO2 pre-packed column
  5. washeluting with 0:1-1:4 EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-90c08de923a14ffc97cb9dfd628ab5e1
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680098B2

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