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

HRID 415932

반응식

HRID 415932 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 15192740ethyl 2,3-dihydro-1-methyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxylate수율 21.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0367d78ef07b45d5a091461dfa2dc7ed
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088794B2

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