3-Acetyl-5-bromopyridine → 3-Bromo-5-(1-hydroxyethyl)pyridine

HRID 2071022Notes

Reaction equation

HRID 2071022 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:10])[CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 8204233-Acetyl-5-bromopyridineHCID 4311764Sodium borohydride

Product 1

HCID 129974353-Bromo-5-(1-hydroxyethyl)pyridineYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(5-bromopyridin-3-yl)ethanone (5.0 g, 25.0 mmol) in anhydrous MeOH (50 mL) at 0° C., was added NaBH4 (1.32 g, 35.0 mmol) and the reaction was allowed to warm to room temperature. All solvent was removed. The residue was dissolved in cold water and extracted with EtOAc (2×70 mL). The combined organic layers was dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (40% EtOAc in hexanes) to provide 4.555 g of 1-(5-bromopyridin-3-yl)ethanol.

Workup

  1. customAll solvent was removed
  2. dissolutionThe residue was dissolved in cold water
  3. extractionextracted with EtOAc (2×70 mL)
  4. dry with materialThe combined organic layers was dried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-583ae12e50e643cbbb0c01bc2fb9b1e6
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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