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

HRID 394815Notes

Reaction equation

HRID 394815 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-10877fc50af445a7b0677e1641ba62fa
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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