Methanol → HCID 20356074, compound

HRID 371738Notes

Reaction equation

HRID 371738 reaction equation
[C:1]1([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH:15]([C:16]([O:18]C(C)C)=[O:17])[C:11]3=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]1([C:6]([C:8]2[N:12]3[CH2:13][CH2:14][CH:15]([C:16]([OH:18])=[O:17])[C:11]3=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 20356153HCID 20356153, compound

Product 1

HCID 20356074HCID 20356074, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 336 mg. of isopropyl 5-(2-thenoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate in 10 ml. of methanol is treated with a solution of 690 mg. of potassium carbonate in 5 ml. of water. The reaction mixture is refluxed under nitrogen atmosphere for 2 hours, cooled, and evaporated to dryness. The residue is taken up in 10 ml. of 10% aqueous hydrochloric acid and 50 ml. of water and the resultant mixture extracted with ethyl acetate (2 × 50 ml.). The combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure. Crystallization of the residue from ethyl acetate affords 5-(2-thenoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid, identical to the product obtained in Example 10 A.

Workup

  1. temperatureThe reaction mixture is refluxed under nitrogen atmosphere for 2 hours
  2. temperaturecooled
  3. customevaporated to dryness
  4. extractionof water and the resultant mixture extracted with ethyl acetate (2 × 50 ml.)
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-584d80dafa15409f93bcc453dbe14838
Source dataset
uspto-grants-1978_05
Patent number
US04087539

Reaction notes

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