Sodium Methoxide → HCID 67239280, compound

HRID 880433Notes

Reaction equation

HRID 880433 reaction equation
[CH3:1][O-:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][N:8]1[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:17]C)=[O:15])[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]1[C:25]([O:27][CH2:28]C)=[O:26]>CO>[CH3:1][O:2][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH3:17])=[O:15])[C:10]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:9]1[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66914769HCID 66914769, compound

Product 1

HCID 67239280HCID 67239280, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (190 mg, 3.50 mmol) was added to a solution of diethyl 1-(3-chloropropyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate (1.1 g, 2.91 mmol) in methanol (10 mL) and stirred at reflux for 28 h. The reaction mixture was cooled to room temperature and concentrated to dryness. The residue was dissolved in water and the aqueous layer was extracted with dichloromethane. The organic layer was washed with water, brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford dimethyl 1-(3-methoxypropyl)-5-methyl-3-phenyl-pyrrole-2,4-dicarboxylate (330 mg, 33%) as a yellow oil. The aqueous layer was acidified with 2N hydrochloric acid to pH 2 and extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over anhydrous sodium sulphate and concentrated to afford 4-methoxycarbonyl-1-(3-methoxypropyl)-5-methyl-3-phenyl-pyrrole-2-carboxylic acid (170 mg, 18%) as a pink oil.

Workup

  1. temperatureat reflux for 28 h
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in water
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4a1897e78d849b6bc7ecf7888ad9ddd
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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