Water → 4-Butylpyridine

HRID 1269100Notes

Reaction equation

HRID 1269100 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[Br-].C([PH3+])CC.[N:12]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.O>C1COCC1>[CH2:18]([C:15]1[CH:16]=[CH:17][N:12]=[CH:13][CH:14]=1)[CH2:1][CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 22600529HCID 22600529, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 1384594-ButylpyridineYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Butylpyridine was prepared by adding potassium-t-butoxide (0.68 g, 6 mmol) to propylphosphonium bromide (Aldrich) (2.4 g, 6.0 mmol) in THF (10 mL), at 0° C. and stirring at room temperature for 1 hour. Pyridine-4-carbaldehyde (428 mg, 4 mmol) was added and the reaction mixture stirred for 2 h. The reaction mixture was then poured into water and extracted with ethyl acetate. The product obtained after removing the solvent was taken as such in methanol (30 mL) to which palladium on carbon (10%, 300 mg) was added and hydrogenated at 1 atm pressure over night. Removal of solvent and purification on column chromatography using ethyl acetate resulted in pure product 4-butylpyridine (500 mg, 92%):

Workup

  1. custom4-Butylpyridine was prepared
  2. stirringthe reaction mixture stirred for 2 h
  3. extractionextracted with ethyl acetate
  4. customThe product obtained
  5. customafter removing the solvent
  6. additionwas added
  7. waithydrogenated at 1 atm pressure over night
  8. customRemoval of solvent and purification on column chromatography

Sources & evidence

ORD record
ord-249ec67247de4371a9d72b953ff98c1b
Source dataset
uspto-grants-2007_04
Patent number
US07199105B2

Reaction notes

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