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

HRID 613032

반응식

HRID 613032 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.[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

참가 물질

7

반응물 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 5271565Dimethyl maleateHCID 220073783,4-Dimethoxy-6-(4-pyridyl) hydroxymethylbenzaldehyde dimethylacetal

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c5a8e07cf650423bbe0c823c8fdf1549
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06005106

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