Methyl triflate → ethyl 2,3-dihydro-1-methyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxylate

HRID 2266344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2266344
[O:1]=[C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.F[C:19](F)(F)S(OC)(=O)=O>ClCCl>[CH3:19][N:4]1[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2](=[O:1])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

4

Edukt 2

HCID 9526Methyl triflateHCID 223722Ethyl 3-oxo-2-phenyl-2,3-dihydro-1h-pyrazole-4-carboxylate

Produkt 1

HCID 15192740ethyl 2,3-dihydro-1-methyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxylateAusbeute 21,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylate (1000 mg, 5.0 mmol) in dichloromethane (10 mL) was added methyl trifluoromethanesulfonate (1200 mg, 7.3 mmol). The red solution was stirred at room temperature. After 14 h, the mixture was partitioned between dichloromethane and NaHCO3 (sat). The aqueous was extracted with dichloromethane (2×). The combined organic was dried over Na2SO4, concentrated and purified on silica. The product was triturated with EtOAc-hexane-CHCl3 to give the pure product as crystals (260 mg, 21%). Calc'd for C12H12N2O3, 232.08; MS (ESI pos. ion) m/z: 233 (MH+). 1H NMR (400 MHz, CHLOROFORM-d): 1.36 (t, J=7.04 Hz, 3H), 3.39 (s, 3H), 4.32 (q, J=7.17 Hz, 2H), 7.32 (d, J=7.43 Hz, 2H), 7.42 (t, J=7.34 Hz, 1H), 7.50 (t, J=7.73 Hz, 2H), 7.99 (s, 1H).

Aufarbeitung

  1. customthe mixture was partitioned between dichloromethane and NaHCO3 (sat)
  2. extractionThe aqueous was extracted with dichloromethane (2×)
  3. dry with materialThe combined organic was dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified on silica
  6. customThe product was triturated with EtOAc-hexane-CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-d851f06a3abc4c6383dc1e85a468481b
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858623B2

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