3-Bromo-4-(hex-1-en-1-yl)pyridine → 3-Bromo-4-hexylpyridine

HRID 2390115Notes

Reaction equation

HRID 2390115 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH3:13]>CCOC(C)=O.[Pt](=O)=O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 1

HCID 670080793-Bromo-4-(hex-1-en-1-yl)pyridine2×

Product 1

HCID 585218843-Bromo-4-hexylpyridine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-4-(hex-1-en-1-yl)pyridine (Intermediate 12; 360 mg; 1.50 mmol) and platinum dioxide (34 mg; 0.15 mmol) in EtOAc (35 mL) was hydrogenated at 7 atm for 1 hour in a PARR apparatus. The reaction mixture was filtered, evaporated and purified by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc, affording the title compound as a colorless liquid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. custompurified by flash column chromatography
  4. washeluting with cyclohexane containing
  5. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-62c1d9b9b9674a1fa1e1a583be010cc2
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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