Hydrochloric Acid → 1-(5-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)ethanone

HRID 2425544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2425544
C(O[CH:4]=[C:5]([C:9](=O)[CH3:10])[C:6](=[O:8])[CH3:7])C.[F:12][C:13]([F:18])([F:17])[CH2:14][NH:15][NH2:16].Cl>CO>[CH3:10][C:9]1[N:15]([CH2:14][C:13]([F:18])([F:17])[F:12])[N:16]=[CH:4][C:5]=1[C:6](=[O:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 787402,2,2-TrifluoroethylhydrazineHCID 2404183-(Ethoxymethylene)pentane-2,4-dione

Produkt 1

HCID 671822581-(5-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)ethanoneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(ethoxymethylene)pentane-2,4-dione (Perkin 1. 2000, 1455-1460, 1.95 g, 12.5 mmol) in MeOH (33 ml) was added a solution of 2,2,2-trifluoroethylhydrazine (1.54 g, 13.5 mmol) and conc.HCl (2.6 ml) in MeOH (10 ml) (pre-cooled at 0° C.) dropwise at −15° C. The resulting mixture was then stirred for 24 h at rt. After removal of the solvent at rt, the residue was basified with 2N NaOH aq, and the aqueous layer was extracted several times with EtOAc. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo to give the crude product as a single regioisomer (1.41 g, 51% yield). 1H NMR (300 MHz, CDCl3) δ 2.46 (3H, s), 2.62 (3H, s), 4.66 (1H, d, J=6.0 Hz), 4.72 (1H, d, J=9.0 Hz), 7.92 (1H, s). MS (ESI) m/z 207 (M+H)+

Aufarbeitung

  1. customdropwise at −15° C
  2. customAfter removal of the solvent at rt
  3. extractionthe aqueous layer was extracted several times with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-785f54ba52934704bac387b914d79a63
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964732B2

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