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

HRID 1743034

Reaction equation

HRID 1743034 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]23O[CH:10]([C:11]4[C:16]2=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=4)[C:9]([C:22]([O:24][CH3:25])=[O:23])=[C:8]3[C:26]([O:28][CH3:29])=[O:27])=[CH:3][CH:2]=1.FB(F)F.C(OCC)C>C(#N)C>[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:22]([O:24][CH3:25])=[O:23])[C:8]=2[C:26]([O:28][CH3:29])=[O:27])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 190062311-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxy-1,4-epoxy-1,4-dihydronaphthalene

Product 1

HCID 117286421-(4-Pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthaleneYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Pyridyl)- 2,3-bis(methoxycarbonyl)-6,7-dimethoxy-1,4-epoxy-1,4-dihydronaphthalene (3.0 g) and trifluoroborane.diethyl ether (1.95 g) are added to acetonitrile (100 ml), and the mixture is refluxed for 2 hours. The reaction solution is separated with a mixture of chloroform (300 ml) and aqueous sodium hydrogen carbonate solution (50 ml), and the organic layer is further washed with aqueous sodium hydrogen carbonate solution, dried, and concentrated. The resulting residue is washed with a small amount of diethyl ether to give 1-(4-pyridyl)-2,3-bis(methoxy-carbonyl)-6,7-dimethoxynaphthalene (2.1 g) as crystal.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customThe reaction solution is separated with a mixture of chloroform (300 ml) and aqueous sodium hydrogen carbonate solution (50 ml)
  3. washthe organic layer is further washed with aqueous sodium hydrogen carbonate solution
  4. customdried
  5. concentrationconcentrated
  6. washThe resulting residue is washed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-1ac07c276e6c413681a20eb07e24fb5f
Source dataset
uspto-grants-1994_08
Patent number
US05342941

Linked notes

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