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

HRID 2216727

反応式

HRID 2216727 の反応式
[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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23994Zinc触媒2 回HCID 24612Mercury dibromide触媒HCID 241Benzene溶媒HCID 962Water溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b0e976d4de05414aae0e9b66c3180f7c
出典データセット
uspto-grants-2006_09
特許番号
US07112638B2

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