Butyllithium → HCID 178435654, compound

HRID 2390796Notes

Reaction equation

HRID 2390796 reaction equation
Br[C:2]1[C:3]([CH2:10][CH3:11])=[N:4][C:5]([OH:9])=[C:6]([Br:8])[CH:7]=1.[Li]CCCC>C1COCC1>[Br:8][C:6]1[C:5]([OH:9])=[N:4][C:3]([CH2:10][CH3:11])=[CH:2][CH:7]=1

Participants

4

Reactant 2

HCID 178418339ButyllithiumHCID 178437766HCID 178437766, compound

Product 1

HCID 178435654HCID 178435654, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

step 5—To a suspension of 30 (320 mg) in THF (10 mL) at −78° C. was added dropwise a solution of n-BuLi (2.0M in cyclohexane, 1.25 mL). The reaction was stirred at −78° C. for 2 h then quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 50% EtOAc) to afford 45 mg of 3-bromo-6-ethyl-2-hydroxy-pyridine (32) as a white solid.

Workup

  1. customthen quenched with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by SiO2 chromatography
  8. washeluting with an EtOAc/hexane gradient (10 to 50% EtOAc)

Sources & evidence

ORD record
ord-81be81cfc0cd4acd9b21b24f610bcd42
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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