Methanol → (E)-3-(4-Amino-phenyl)-2-methyl-acrylic acid methyl ester

HRID 723634

反応式

HRID 723634 の反応式
[CH3:1][C:2](=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[CH3:16]O>CCOC(C)=O.CCOCC.CC(O)=O>[CH3:16][O:5][C:3](=[O:4])/[C:2](/[CH3:1])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1

参加物

6

反応物 2

HCID 887MethanolHCID 235115alpha-Methyl-4-nitrocinnamic acid

生成物 1

HCID 57802977(E)-3-(4-Amino-phenyl)-2-methyl-acrylic acid methyl ester

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

α-Methyl-4-nitrocinnamic acid (53 mg, 0.25 mmol) was dissolved in EtOAc and MeOH and a solution of CH2N2 in Et2O was added until a persistent yellow color was observed. A couple of drops of AcOH were added to destroy the excess CH2N2. The mixture was diluted with EtOAc and the organic layer was washed with H2O, aqueous NaOH (1N) and brine, dried over anhydrous MgSO4 and concentrated to dryness. The residue was re-dissolved in EtOH (2 mL), SnCl22H2O (289 mg, 1.28 mmol) was added and the reaction mixture was heated to reflux for 1 h. The mixture was cooled to RT, diluted with EtOAc and quenched by the addition of aqueous, saturated NaHCO3. The organic layer was separated, washed with brine, dried over anhydrous MgSO4 and concentrated to dryness to give the title compound (40 mg) as a yellow solid.

後処理

  1. customto destroy the excess CH2N2
  2. additionThe mixture was diluted with EtOAc
  3. washthe organic layer was washed with H2O, aqueous NaOH (1N) and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue was re-dissolved in EtOH (2 mL)
  7. additionSnCl22H2O (289 mg, 1.28 mmol) was added
  8. temperaturethe reaction mixture was heated
  9. temperatureto reflux for 1 h
  10. additiondiluted with EtOAc
  11. customquenched by the addition of aqueous, saturated NaHCO3
  12. customThe organic layer was separated
  13. washwashed with brine
  14. dry with materialdried over anhydrous MgSO4
  15. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-edcb267c6a464afca1288407d8c1fd36
出典データセット
uspto-grants-2006_11
特許番号
US07141574B2

関連ノート

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