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

HRID 1366816

반응식

HRID 1366816 반응식
[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.O.O.Cl[Sn]Cl>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

참가 물질

7

반응물 3

HCID 887MethanolHCID 61436Stannous chloride dihydrateHCID 235115alpha-Methyl-4-nitrocinnamic acid

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매2회

실험 절차

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), SnCl2.2H2O (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.

후처리

  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. temperaturethe reaction mixture was heated
  8. temperatureto reflux for 1 h
  9. customquenched by the addition of aqueous, saturated NaHCO3
  10. customThe organic layer was separated
  11. washwashed with brine
  12. dry with materialdried over anhydrous MgSO4
  13. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-9a3c3518b1c5446aab9cd6b21b0f5a60
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893084B2

연결된 노트

불러오는 중…