Methanesulfonic Acid → 1-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene

HRID 1743035

반응식

HRID 1743035 반응식
CO[CH:3](OC)[C:4]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:8][C:7]([O:16][CH3:17])=[C:6]([O:18][CH3:19])[C:5]=1CO.[C:24]([O:32][CH3:33])(=[O:31])/[CH:25]=[CH:26]\[C:27]([O:29][CH3:30])=[O:28].[CH3:34]S(O)(=O)=O>C(O)(=O)C.C1(C)C=CC=CC=1>[N:13]1[CH:12]=[CH:11][C:10]([C:9]2[C:4]3[C:3](=[CH:8][C:7]([O:16][CH3:17])=[C:6]([O:18][CH3:19])[CH:5]=3)[CH:34]=[C:26]([C:27]([O:29][CH3:30])=[O:28])[C:25]=2[C:24]([O:32][CH3:33])=[O:31])=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 5271565Dimethyl maleateHCID 220073783,4-Dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal

생성물 1

HCID 117286421-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene수율 62.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

To a solution of 3,4-dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal (18.4 g) in a mixture of acetic acid (50 ml) and toluene (50 ml) is added dimethyl maleate (8.64 ml), and the mixture is refluxed for one hour. To the mixture is added methanesulfonic acid (9.33 ml), and the mixture is refluxed for 8 hours while removing the resulting water with a Dean-Stalk apparatus. The mixture is cooled to room temperature, and concentrated. The residue is dissolved in chloroform, and the pH value thereof is adjusted with aqueous potassium carbonate solution to pH 8. The mixture is extracted twice with each 100 ml of chloroform, and the extracts are washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting residue is crystallized from diethyl ether to give a diester compound, 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (13.5 g).

후처리

  1. temperaturethe mixture is refluxed for one hour
  2. temperaturethe mixture is refluxed for 8 hours
  3. customwhile removing the resulting water with a Dean-Stalk apparatus
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in chloroform
  6. extractionThe mixture is extracted twice with each 100 ml of chloroform
  7. washthe extracts are washed with a saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe resulting residue is crystallized from diethyl ether

출처 및 근거

ORD 기록
ord-ea6e579a5bde40b8844841c48e68995a
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05342941

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