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

HRID 1743035

反応式

HRID 1743035 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ea6e579a5bde40b8844841c48e68995a
出典データセット
uspto-grants-1994_08
特許番号
US05342941

関連ノート

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