Thiophene → HCID 11521158, compound

HRID 485067Notes

Reaction equation

HRID 485067 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[C:11]([O:16]CC)(=[O:15])[C:12]([CH3:14])=[O:13].[Cl-].[NH4+]>CCCCCC.C(OCC)C>[OH:13][C:12]([C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)([CH3:14])[C:11]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 12041Ethyl pyruvateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 11521158HCID 11521158, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1.6 molar solution of n-butyl-lithium in hexane (37 ml.) was added to a solution of thiophene (5 g.) in diethyl ether (50 ml.) which was maintained at 0° C., and the mixture was heated under reflux for 6 hours and then cooled to -78° C. A solution of ethyl pyruvate (5.9 g.) in diethyl ether (20 ml.) was added dropwise, the mixture was allowed to warm up to laboratory temperature and saturated aqueous ammonium chloride solution (20 ml.) was added. The mixture was extracted with ethyl acetate and the organic extract was washed with water and then with saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated to dryness. The residue was dissolved in ethanol (30 ml.), a solution of potassium hydroxide (1.4 g.) in water (5 ml.) was added and the mixture was stirred at laboratory temperature for 2 hours and then evaporated to dryness. The residue was washed with ethyl acetate, dilute aqueous hydrochloric acid was added and the mixture was extracted with ethyl acetate. The extract was washed with water and then saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated to dryness. There was thus obtained as residue 2-hydroxy-2-(thien-2-yl)propionic acid, which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperaturecooled to -78° C
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionthe organic extract
  7. washwas washed with water
  8. dry with materialwith saturated aqueous sodium chloride solution, dried over magnesium sulphate
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in ethanol (30 ml.)
  11. additiona solution of potassium hydroxide (1.4 g.) in water (5 ml.) was added
  12. customevaporated to dryness
  13. washThe residue was washed with ethyl acetate, dilute aqueous hydrochloric acid
  14. additionwas added
  15. extractionthe mixture was extracted with ethyl acetate
  16. washThe extract was washed with water
  17. dry with materialsaturated aqueous sodium chloride solution, dried over magnesium sulphate
  18. customevaporated to dryness

Sources & evidence

ORD record
ord-27328f2ac0cb489c808bb1d72606726a
Source dataset
uspto-grants-1985_08
Patent number
US04535092

Reaction notes

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