Ethyl 2-bromopropionate → 2-Methyl-3-(4-methyl-5-phenyl-2-thienyl)-acrylic acid

HRID 2216727

Reaktionsgleichung

Reaktionsgleichung von HRID 2216727
[CH:1]([C:3]1[S:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:8])[CH:7]=1)=O.C([O:17][C:18](=[O:22])[CH:19](Br)[CH3:20])C>C1C=CC=CC=1.O.[Zn].[Hg](Br)Br>[CH3:20][C:19](=[CH:1][C:3]1[S:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:8])[CH:7]=1)[C:18]([OH:22])=[O:17]

Komponenten

7

Edukt 2

HCID 79040Ethyl 2-bromopropionateHCID 123232534-Methyl-5-phenylthiophene-2-carbaldehyde

Produkt 1

HCID 671746362-Methyl-3-(4-methyl-5-phenyl-2-thienyl)-acrylic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysator2×HCID 24612Mercury dibromideKatalysatorHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 2-formyl-4-methyl-5-phenylthiophene (20.2 g, 0.1 mol) and ethyl-2-bromopropionate (0.12 mol, 15.5 mL) was added to a suspension of Zn (7 g, 0.1 mol) in 150 mL of benzene with a catalytic amount of HgBr2. The resulting mixture was refluxed under stirring while all amount of Zn will not be dissolved, and subsequently dissolved in water. The organic layer was isolated, washed with a 10% aq. solution of HCl, dried over MgSO4 and evaporated off to dryness. The residue, corresponding to 2-methyl-3-(4-methyl-5-phenyl-2-thienyl)ethyl acrylate, was used without further purification in the synthesis of the related acid. In fact, it was added to a 30% aq. solution of sodium hydroxide in 100 mL of ethanol and refluxed for 2 h. The resulting reaction mixture was diluted in water, acidified and filtered. The precipitate was dried under P2O5. Yield 16.7 g (65%).

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed
  2. dissolutionbe dissolved
  3. customThe organic layer was isolated
  4. washwashed with a 10% aq. solution of HCl
  5. dry with materialdried over MgSO4
  6. customevaporated off to dryness
  7. customThe residue, corresponding to 2-methyl-3-(4-methyl-5-phenyl-2-thienyl)ethyl acrylate, was used without further purification in the synthesis of the related acid
  8. additionIn fact, it was added to a 30% aq. solution of sodium hydroxide in 100 mL of ethanol
  9. temperaturerefluxed for 2 h
  10. customThe resulting reaction mixture
  11. filtrationfiltered
  12. customThe precipitate was dried under P2O5

Quellen und Nachweise

ORD-Eintrag
ord-b0e976d4de05414aae0e9b66c3180f7c
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07112638B2

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