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

HRID 1743030

Reaction equation

HRID 1743030 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a8ca16ee622e4d3780416f0149f58f03
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Linked notes

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