Sodium Hydroxide → 3,5-dimethyl-1H-pyrrole-2-carboxylic acid

HRID 490328

Reaction equation

HRID 490328 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([O:10]CC)=[O:9].[OH-].[Na+]>C1COCC1.O.CO.O>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 1374771H-Pyrrole-2-carboxylic acid, 3,5-dimethyl-, ethyl ester

Product 1

HCID 27764683,5-dimethyl-1H-pyrrole-2-carboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 3,5-dimethyl-2-pyrrolecarboxylate (Aldrich) (504 mg, 3 mmol) in THF/H2O/MeOH (5:1:1, 30 ml) was added NaOH (480 mg, 12 mmol) in H2O (12 ml). The mixture was stirred at 75° C. overnight. The homogeneous mixture was washed with ether. To the aqueous layer was added a saturated aqueous KHSO4 solution until the pH was about 3. The solution was then extracted with dichloromethane. The extracts were dried over MgSO4 and evaporated. The residue was purified on silica (ethylacetate/methanol 90/10) to give the title compound (375 mg, 90%).

Workup

  1. washThe homogeneous mixture was washed with ether
  2. additionTo the aqueous layer was added a saturated aqueous KHSO4 solution until the pH was about 3
  3. extractionThe solution was then extracted with dichloromethane
  4. dry with materialThe extracts were dried over MgSO4
  5. customevaporated
  6. customThe residue was purified on silica (ethylacetate/methanol 90/10)

Sources & evidence

ORD record
ord-affd9ab03d1a41febbd17463c5b02f33
Source dataset
uspto-grants-2009_05
Patent number
US07528156B2

Linked notes

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