Methanol → HCID 13487034, compound

HRID 372226Notes

Reaction equation

HRID 372226 reaction equation
[C:1]1([CH3:23])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([O:19]C(C)C)=[O:18])[C:12]3=[CH:11][CH:10]=2)=[O:8])=[CH:3][CH:2]=1.CO.[OH-].[Na+]>O>[C:1]1([CH3:23])[CH:2]=[CH:3][C:4]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]3=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13486973HCID 13486973, compound

Product 1

HCID 13487034HCID 13487034, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 250 mg. of isopropyl 5-p-toluoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate in 8 ml. of methanol is treated under an atmosphere of nitrogen, with a solution of 200 mg. of sodium hydroxide in 1 ml. of water, maintaining the reaction mixture at room temperature for 1.5 hours. The methanol is then removed under reduced pressure and the basic solution which remains is diluted with 5 ml. of water and extracted with ether to remove any unsaponifiable product. The aqueous solution is acidified with 10% hydrochloric acid and extracted three times with ethyl acetate. The combined extracts are dried and evaporated to dryness under reduced pressure, and the residue crystallized from ethyl acetate-hexane, to give 5-p-toluoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid, identical to the product obtained in Example 9.

Workup

  1. customThe methanol is then removed under reduced pressure
  2. additionthe basic solution which remains is diluted with 5 ml
  3. extractionof water and extracted with ether
  4. customto remove any unsaponifiable product
  5. extractionextracted three times with ethyl acetate
  6. customThe combined extracts are dried
  7. customevaporated to dryness under reduced pressure
  8. customthe residue crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bc69c7aa410a48189f2439935a5641b9
Source dataset
uspto-grants-1978_05
Patent number
US04089969

Reaction notes

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