Sodium ethoxide → 1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole

HRID 610159노트

반응식

HRID 610159 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[O-]CC.[Na+].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][N:27]=[C:28](Br)[C:29]([F:32])([F:31])[F:30])=[CH:22][CH:21]=1>C(O)C>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:28]([C:29]([F:30])([F:31])[F:32])=[N:27]2)=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 2759240Ethyl 3-(fur-2-yl)-3-oxopropanoateHCID 713581942,2,2-Trifluoro-N-(4-methoxyphenyl)ethanehydrazonoyl bromide

생성물 1

HCID 179399581-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole수율 61%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of ethyl 3-(2-furyl)-3-ketopropionate (2.45 g, 13.4 mmol) in 20 mL of absolute ethanol was added sodium ethoxide (4.6 mL of a 21% weight solution in ethanol, 12.2 mmol) followed by 2, 2, 2-trifluoroacetoyl bromide -N-(4-methoxyphenyl)hydrazone (1.82 g, 6.1 mmol). This mixture was stirred at ambient temperature for 4 h. The volatiles were removed in vacuo and the residue was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by recrystallization from hexane/ethyl acetate to afford 1.4 g (61%) of the title compound. LRMS (ES+): 381.2 (M+H)+.

후처리

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-76f6df113bec4d51b0b28c681a9da79b
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998424

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