Triethylamine → 5-Bromo-2-(3-methoxypropyl)pyridine

HRID 1251125Notes

Reaction equation

HRID 1251125 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1.C(N(CC)CC)C>C(O)C.[H][H].[Pt]=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH3:12])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 225032615-Bromo-2-(3-methoxy-prop-1-ynyl)-pyridine

Product 1

HCID 225024945-Bromo-2-(3-methoxypropyl)pyridineYield 69.4%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

5-Bromo-2-(3-methoxypropynyl)pyridine (5.652 g) was dissolved in ethanol (150 ml), followed by the addition of triethylamine (2.5 ml) and platinum oxide (230 mg), and the resulting mixture was stirred in hydrogen atmosphere at room temperature for 5 hr. After the platinum oxide was filtered off, the resulting mixture was evaporated and partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (3.991 g, yield; 68%).

Workup

  1. filtrationAfter the platinum oxide was filtered off
  2. customthe resulting mixture was evaporated
  3. custompartitioned between ethyl acetate and water
  4. washThe resulting organic layer was washed with water
  5. dry with materialdried (over MgSO4)
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-868cc9df460448e09fccc1b2c04ea2b2
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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