Sodium borohydride → 4-Bromopyridine-2,6-dimethanol

HRID 636313Notes

Reaction equation

HRID 636313 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([C:10](OCC)=[O:11])[N:7]=[C:6]([C:15](OCC)=[O:16])[CH:5]=1>CCO>[Br:3][C:4]1[CH:9]=[C:8]([CH2:10][OH:11])[N:7]=[C:6]([CH2:15][OH:16])[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13794409Diethyl 4-bromopyridine-2,6-dicarboxylate

Product 1

HCID 6428174-Bromopyridine-2,6-dimethanolYield 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized via modification of Acta Chem. Scand. B42, 373, 1988. A mixture of NaBH4 (6.8 g, 180 mmol), diethyl 4-bromopyridine-2,6-dicarboxylate (12.1 g, 40 mmol) in absolute EtOH (500 mL) was heated under reflux for 18 h. The solvent was removed in vacuo and the residue was treated with hot saturated aqueous NaHCO3. The mixture was extracted with EtOAc, the combined organic phase was dried (Na2SO4) and evaporated. The dried material was recrystallized from EtOAc to give 7.3 g (83%) of the title compound as white crystals.

Workup

  1. customThe title compound was synthesized via modification of Acta Chem
  2. temperaturewas heated
  3. temperatureunder reflux for 18 h
  4. customThe solvent was removed in vacuo
  5. additionthe residue was treated with hot saturated aqueous NaHCO3
  6. extractionThe mixture was extracted with EtOAc
  7. dry with materialthe combined organic phase was dried (Na2SO4)
  8. customevaporated
  9. customThe dried material was recrystallized from EtOAc

Sources & evidence

ORD record
ord-8c8ec38964ea472eb33ec9e13580ccc4
Source dataset
uspto-grants-2001_02
Patent number
US06191273B1

Reaction notes

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