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

HRID 2216727

반응식

HRID 2216727 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 23994Zinc촉매2회HCID 24612Mercury dibromide촉매HCID 241Benzene용매HCID 962Water용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b0e976d4de05414aae0e9b66c3180f7c
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112638B2

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