Hydrochloric Acid → 3-[2,2′-Bithiophen]-5-yl-2-propenoic acid

HRID 1291592Notes

Reaction equation

HRID 1291592 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>O.N1C=CC=CC=1>[C:15]([CH:14]=[CH:1][C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 364428[2,2'-Bithiophene]-5-carboxaldehyde

Product 1

HCID 572037503-[2,2′-Bithiophen]-5-yl-2-propenoic acidYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

3.88 g of 5-formyl-2,2'-bithiophene, 4.16 g of malonic acid, 15.5 ml of pyridine and 1.4 g of piperidine were heated and stirred at 90° C. in oil bath for 2 hours. Then raised the temperature to 120° C. for 10 minutes. The reaction mixture was cooled down to room temperature and diluted with 100 ml of distilled water. 40 ml of concentrated HCl was added to acidify the solution. The orange precipitate thus crystallized was further purified by silica gel chromatography. From the eluate of acetone/n-hexane (2/5), 2.95 g of product was thus obtained and the melting point thereof was 175° C. (M+ : 236). 0.16 g of pure 5-(2-dicarboxy-ethenyl)-2,2'-bithiophene was also obtained and the melting point thereof was 220°-221° C.

Workup

  1. temperatureThen raised the temperature to 120° C. for 10 minutes
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. customThe orange precipitate thus crystallized
  4. customwas further purified by silica gel chromatography

Sources & evidence

ORD record
ord-e2edb3f034254cd4bd76bd515c59d922
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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