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

HRID 610159Notes

Reaction equation

HRID 610159 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-76f6df113bec4d51b0b28c681a9da79b
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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