Cyclohexanone → 6-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 1442541Notes

Reaction equation

HRID 1442541 reaction equation
[S:1]1[C:8]2[CH:7]=[CH:6][NH:5][C:4]=2[CH:3]=[C:2]1[C:9]([O:11]C)=[O:10].[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CO.C[O-].[Na+]>CO>[C:13]1([C:7]2[C:8]3[S:1][C:2]([C:9]([OH:11])=[O:10])=[CH:3][C:4]=3[NH:5][CH:6]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 12110979methyl 4H-thieno(3,2-b)pyrrole-2-carboxylateHCID 23694274Sodium methanolate methanol

Product 1

HCID 586790836-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acidYield 101.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate (12 g, 68 mmol) and cyclohexanone (21 ml, 204 mmol) in methanol (300 ml) was added 28% sodium methoxide methanol solution (100 ml) and the mixture was stirred with heating under reflux for 2 days. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. 6N Hydrochloric acid (100 ml) was added and the precipitated solid was collected by filtration. The solid was washed successively with water (300 ml×5) and n-hexane (300 ml×3), and dried under reduced pressure to give 6-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid (17 g, yield 100%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 days
  3. concentrationconcentrated under reduced pressure
  4. addition6N Hydrochloric acid (100 ml) was added
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe solid was washed successively with water (300 ml×5) and n-hexane (300 ml×3)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc9060bee5e3496d850677ddd86912df
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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