Methanol → HCID 10811188, compound

HRID 324010Notes

Reaction equation

HRID 324010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([C:22](OC)=[O:23])[C:9]=2[C:26](OC)=[O:27])[N:3]=1.[BH4-].[Li+].CO>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([CH2:22][OH:23])[C:9]=2[CH2:26][OH:27])[N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 10623819HCID 10623819, compound

Product 1

HCID 10811188HCID 10811188, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1-(2-bromo-6-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (715 mg) in tetrahydrofuran (20 ml) is added lithium borohydride (174 mg), and the mixture is refluxed. To the mixture is added dropwise a mixture of methanol (2.2 ml) and tetrahydrofuran (10 ml) under reflux over a period of two hours. After the reaction is complete, the mixture is concentrated under reduced pressure to remove the solvent, and ethyl acetate and water are added to the residue. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=15:1) to give 1-(2-bromo-6-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (505 mg).

Workup

  1. temperaturethe mixture is refluxed
  2. additionTo the mixture is added dropwise
  3. temperatureunder reflux over a period of two hours
  4. concentrationthe mixture is concentrated under reduced pressure
  5. customto remove the solvent, and ethyl acetate and water
  6. additionare added to the residue
  7. customThe ethyl acetate layer is separated
  8. washwashed
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customto remove the solvent
  12. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-db12649a6aec4e04a90f5bf6c5595100
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Reaction notes

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