Hydrochloric Acid → 1-(2-Benzyl-4-pyridyl)-4-methyl-1-pentanone

HRID 660036Notes

Reaction equation

HRID 660036 reaction equation
[Mg].Br[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].[CH2:8]([C:15]1[CH:20]=[C:19]([C:21]#N)[CH:18]=[CH:17][N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[OH-:24].[Na+]>BrC=CBr.CCOCC>[CH2:8]([C:15]1[CH:20]=[C:19]([C:21](=[O:24])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6])[CH:18]=[CH:17][N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 78911-Bromo-3-methylbutaneHCID 14798Sodium HydroxideHCID 5462224MagnesiumHCID 135718142-Benzylisonicotinonitrile

Product 1

HCID 249617181-(2-Benzyl-4-pyridyl)-4-methyl-1-pentanoneYield 58%

Reagents, catalysts & solvents 2

HCID 108971,2-DibromoetheneCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

Anhydrous Et2O (15 mL) was added to magnesium turnings (0.310 g, 12.8 mmol) in a flame-dried flask. Addition of one drop of dibromoethylene was followed by slow addition of 1-bromo-3-methylbutane (1.619 g, 10.7 mmol) in 10 mL of anhydrous Et2O at a rate that kept the reaction mixture under reflux. Once the addition was completed the reaction was refluxed for 1 h and cooled to RT. The mixture was then added via cannula to a solution of 2-benzyl-4-cyanopyridine (1.000 g, 5.1 mmol) in 15 mL of anhydrous Et2O at 0° C. The mixture was stirred at RT for 30 min. and then refluxed for 3 h. The solution was cooled down to RT, poured into 200 mL of 0.5M HCl, and stirred for 30 min. A solution of 1M NaOH was added dropwise until the solution reached pH 9 and the resulting mixture was then extracted with ether (×3), dried with Na2SO4 and concentrated under vacuum. The resulting dark oil was purified by flash chromatography using 1:4 EtOAc/Hexane to give a brown oil (0.801 g, 58%)

Workup

  1. temperatureunder reflux
  2. additionOnce the addition
  3. temperaturewas refluxed for 1 h
  4. temperaturerefluxed for 3 h
  5. temperatureThe solution was cooled down to RT
  6. stirringstirred for 30 min
  7. extractionthe resulting mixture was then extracted with ether (×3)
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated under vacuum
  10. customThe resulting dark oil was purified by flash chromatography

Sources & evidence

ORD record
ord-1d5e723042fc44c287eaacf34dce02f1
Source dataset
uspto-grants-2011_12
Patent number
US08084471B2

Reaction notes

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