ethyl 3-{(1E)-3-[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]prop-1-enyl}benzoate → 3-{(1E)-3-[2-(4-Methylbenzoyl)-1H-pyrrol-1-yl]prop-1-enyl}benzoic acid

HRID 31549Notes

Reaction equation

HRID 31549 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[N:9]([CH2:13]/[CH:14]=[CH:15]/[C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH:10]=[CH:11][CH:12]=2)=[O:7])=[CH:4][CH:3]=1>[OH-].[Li+].C1COCC1.CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[N:9]([CH2:13]/[CH:14]=[CH:15]/[C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH:10]=[CH:11][CH:12]=2)=[O:7])=[CH:27][CH:28]=1

Participants

5

Reactant 1

HCID 23116960ethyl 3-{(1E)-3-[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]prop-1-enyl}benzoate

Product 1

HCID 231169763-{(1E)-3-[2-(4-Methylbenzoyl)-1H-pyrrol-1-yl]prop-1-enyl}benzoic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-{(1E)-3-[2-(4-methylbenzoyl)-1H-pyrrol-1-yl]prop-1-enyl}benzoate (1.94 g) in 1N aqueous lithium hydroxide solution (10 ml), THF (10 ml) and methanol (10 ml) were stirred at 50° C. for 3 hours. Methanol and THF in the reaction solution were evaporated under reduced pressure, and the residue was diluted with water, and washed with diethyl ether. The aqueous layer was acidified with diluted hydrochloric acid solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.66 g, yield for 2 steps: 93%).

Workup

  1. customMethanol and THF in the reaction solution were evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. washwashed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0f8edc27fe24bc29221ebb44799d46e
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Reaction notes

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