Sodium Methoxide → HCID 18177265, compound

HRID 394791Notes

Reaction equation

HRID 394791 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]([O:10]CC)=[O:9])[N:5]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:4]=1.[CH3:21][O-:22].[Na+]>CO.O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([N:5]2[C:6]([C:8]([OH:10])=[O:9])=[CH:7][C:3]([CH2:2][O:22][CH3:21])=[N:4]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 18177282HCID 18177282, compound

Product 1

HCID 18177265HCID 18177265, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 3-(bromomethyl)-1-(4-methoxyphenyl)-1H-pyrazole-5-carboxylate (0.50 g, 1.47 mmol) is dissolved in 12 mL of 0.5 M NaOMe in methanol and heated to reflux for 14 hours. The reaction mixture was cooled and reduced to {fraction (1/10)} original volume. The reaction mixture was dissolved in 20 mL of water and extracted with EtOAc. The aqueous mixture was acidified with 1N HCl and extracted with EtOAc to give 0.236 g (61%) of desired product. A mixture of ethyl and methyl esters (˜0.05 g) was found in the first EtOAc extract. 1H NMR (CDCl3): δ 7.32 (d, J=8.8, 2H); 7.11 (s, 1H); 6.94 (d, J=8.8, 2H); 4.54 (s, 2H); 3.85 (s, 3H); 3.44 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 14 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with EtOAc
  5. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-81eb494c16244ec29800c06ea9b84d31
Source dataset
uspto-grants-2003_08
Patent number
US06602895B2

Reaction notes

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