HCID 13910822, compound → HCID 13910825, compound

HRID 1460216Notes

Reaction equation

HRID 1460216 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:29][CH3:30])=[C:18]([O:21]CC4C=CC=CC=4)[CH:19]=3)[C:14]([OH:31])=[C:13]([C:32]([O:34][CH3:35])=[O:33])[C:12]=2[C:36]([O:38][CH3:39])=[O:37])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>O1CCCC1.CO.[H][H].[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:29][CH3:30])=[C:18]([OH:21])[CH:19]=3)[C:14]([OH:31])=[C:13]([C:32]([O:34][CH3:35])=[O:33])[C:12]=2[C:36]([O:38][CH3:39])=[O:37])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 1

HCID 13910822HCID 13910822, compound

Product 1

HCID 13910825HCID 13910825, compoundYield 90.3%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

2 g of 1-(3,4-dimethoxyphenyl)-2,3-bis(methoxycarbonyl)-4-hydroxy-6-methoxy-7-benzyloxynaphthalene obtained in Example 6 are dissolved in a mixture of 200 ml of tetrahydrofuran and 50 ml of methanol. The solution is stirred in the presence of 2 g of 10% palladium-charcoal in hydrogen atmosphere at 40 psi for 2 hours. After the reaction, the catalyst is removed by filtration, and the filtrate is evaporated to dryness under reduced pressure. The resultant crude crystals are triturated with methanol, whereby 1.5 g of 1-(3,4-dimethoxyphenyl)-2,3-bis(methoxycarbonyl)-4-hydroxy-6-methoxy-7-hydroxynaphthalene is obtained.

Workup

  1. customAfter the reaction
  2. customthe catalyst is removed by filtration
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. customThe resultant crude crystals are triturated with methanol

Sources & evidence

ORD record
ord-7169e58a35fa44e4b0c4504cf65f41a7
Source dataset
uspto-grants-1991_12
Patent number
US05070103

Reaction notes

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