HCID 86736134, compound → HCID 20377673, compound

HRID 1703488Notes

Reaction equation

HRID 1703488 reaction equation
[S:1]1[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=[C:2]1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17](C)([C:23]([O-])=O)[C:18]([O:20]CC)=[O:19])=[CH:13][CH:12]=1)=[O:10]>[OH-].[Na+].C(O)C.O>[S:1]1[C:5]2[S:6][CH:7]=[CH:8][C:4]=2[CH:3]=[C:2]1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 1

HCID 86736134HCID 86736134, compound

Product 1

HCID 20377673HCID 20377673, compoundYield 74.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 2-{4-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}-2-methyl-malonate (16.23 g) is suspended in a mixture of 5% (w/v) aqueous sodium hydroxide solution (90 cc) and ethanol (90 cc), and the suspension is heated at the boiling point for 3 hours. After cooling, the reaction mixture is diluted with distilled water (1000 cc), and then extracted three times with diethyl ether (total 600 cc). The aqueous phase is filtered off, acidified to pH 1 by the addition of a 5N aqueous hydrochloric acid solution and extracted three times with diethyl ether (total 600 cc). The combined ether solutions are washed three times with distilled water (total 300 cc), dried over anhydrous sodium sulphate, decolourizing charcoal (1 g) is added, and the solutions are filtered and evaporated. Crude 2-{4-(thieno[2,3-b]thien-2-yl)carbonyl-phenyl}propionic acid (9.9 g), melting at 150° C., is thus obtained.

Workup

  1. temperaturethe suspension is heated at the boiling point for 3 hours
  2. temperatureAfter cooling
  3. extractionextracted three times with diethyl ether (total 600 cc)
  4. filtrationThe aqueous phase is filtered off
  5. additionacidified to pH 1 by the addition of a 5N aqueous hydrochloric acid solution
  6. extractionextracted three times with diethyl ether (total 600 cc)
  7. washThe combined ether solutions are washed three times with distilled water (total 300 cc)
  8. dry with materialdried over anhydrous sodium sulphate
  9. additionis added
  10. filtrationthe solutions are filtered
  11. customevaporated

Sources & evidence

ORD record
ord-b73eae8bf9834cbe8d1b5faa895f042d
Source dataset
uspto-grants-1978_11
Patent number
US04124596

Reaction notes

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