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

HRID 1743030

反応式

HRID 1743030 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH:10]=[C:9]([C:21](OC)=[O:22])[C:8]=2[C:25](OC)=[O:26])=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH:10]=[C:9]([CH2:21][OH:22])[C:8]=2[CH2:25][OH:26])=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 117286421-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthaleneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 220074131-(4-Pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (2.0 g) in tetrahydrofuran (50 ml) is added dropwise to a suspension of lithium aluminum hydride (100 mg) in tetrahydrofuran (20 ml) at -20° C. The mixture is stirred under ice-cooling for one hour, and thereto are added water (0.1 ml) and 15% aqueous sodium hydroxide solution (0.1 ml). Ten minutes thereafter, water (0.3 ml) is added to the reaction mixture, and the mixture is stirred at room temperature for one hour. The insoluble materials are removed by filtration on celite, and the filtrate is concentrated. The residue is recrystallized from a mixture of ethyl acetate and diethyl ether (1:1) to give 1-(4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (1.35 g).

後処理

  1. temperaturecooling for one hour
  2. stirringthe mixture is stirred at room temperature for one hour
  3. customThe insoluble materials are removed by filtration on celite
  4. concentrationthe filtrate is concentrated
  5. customThe residue is recrystallized from a mixture of ethyl acetate and diethyl ether (1:1)

出典と根拠

ORDレコード
ord-a8ca16ee622e4d3780416f0149f58f03
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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