Sodium Methoxide → HCID 18177265, compound

HRID 610133Notes

Reaction equation

HRID 610133 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 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): δ7.32 (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-d98629a49cab4ac483dc3a5a7ad5a48d
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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