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

HRID 613032

反応式

HRID 613032 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.[CH3:24][O:25][C:26](=[O:33])/[CH:27]=[CH:28]\[C:29]([O:31][CH3:32])=[O:30].[CH3:34]S(O)(=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:27]([C:26]([O:25][CH3:24])=[O:33])[C:28]=2[C:29]([O:31][CH3:32])=[O:30])=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 962WaterHCID 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

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 dimethyl acetal (18.4 g) in a mixture of acetic acid (50 ml) and toluene (50 ml) is added maleic acid dimethyl ester (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 the generated water is removed by using a Dean-stark apparatus. The mixture is cooled to room temperature and concentrated. The residue is dissolved in chloroform, and the pH value thereof is adjusted to pH 8 with an aqueous potassium carbonate solution. The mixture is extracted with chloroform, and the extract is washed, dried, concentrated, and the residue is crystallized from ether to give 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. customis removed
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in chloroform
  5. extractionThe mixture is extracted with chloroform
  6. washthe extract is washed
  7. customdried
  8. concentrationconcentrated
  9. customthe residue is crystallized from ether

出典と根拠

ORDレコード
ord-c5a8e07cf650423bbe0c823c8fdf1549
出典データセット
uspto-grants-1999_12
特許番号
US06005106

関連ノート

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