Tetrahydrofuran → (E)-3-bromo-5-(3-methylbut-1-enyl)pyridine

HRID 2070933Notes

Reaction equation

HRID 2070933 reaction equation
[Li]C[CH2:3][CH2:4][CH3:5].[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([CH:14]=1)[CH:12]=O.[CH2:15]1COCC1>>[Br:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11](/[CH:12]=[CH:15]/[CH:4]([CH3:3])[CH3:5])[CH:14]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 68670697(E)-3-bromo-5-(3-methylbut-1-enyl)pyridine

Conditions

Temperature
0 °C

Procedure

To a stirring mixture of 4.26 g (10.7 mmol) of Ph3PCH2CH(CH3)2Br in 20 mL of THF O° C. was added 12.0 mL of n-BuLi (1.6 M in hexanes). The mixture was stirred at 0° C. for 1 h, and then 521 mg (2.82 mmol) of 5-bromonicotinaldehyde in 20 mL of THF was added. After 5-10 min. the bath was removed and stirring was continued with warming to r.t. After 1 h, the reaction was quenched with water and diluted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography 15% EtOAc/hexanes provided (E)-3-bromo-5-(3-methylbut-1-enyl)pyridine and impurity.

Workup

  1. customAfter 5-10 min. the bath was removed
  2. stirringstirring
  3. temperaturewith warming to r.t
  4. waitAfter 1 h
  5. customthe reaction was quenched with water
  6. additiondiluted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash silica gel chromatography 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-5623a296982049b9ae37271cbc3c2c21
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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