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

HRID 415887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 415887
[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, 3 H), 3.39 (s, 3 H), 4.32 (q, J=7.17 Hz, 2 H), 7.32 (d, J=7.43 Hz, 2 H), 7.42 (t, J=7.34 Hz, 1 H), 7.50 (t, J=7.73 Hz, 2 H), 7.99 (s, 1 H).

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-4c03e7a3bcd84b97bd1c3d9a3a8477fd
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088794B2

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