Ammonium Chloride → (2-Isobutylpyridin-3-yl)methanol

HRID 384120Notes

Reaction equation

HRID 384120 reaction equation
Br[C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:10]([Mg]Br)[CH:11]([CH3:13])[CH3:12].[Cl-].[NH4+]>O1CCCC1>[CH2:10]([C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14761460(2-Bromopyridin-3-yl)methanolHCID 178418816HCID 178418816, compound

Product 1

HCID 68431417(2-Isobutylpyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-bromopyridin-3-yl)methanol (100 mg) in tetrahydrofuran (1 ml), 36 mg of dichloro(1,1′-bis(diphenylphosphino)ferrocene)nickel(II) and 0.8 ml of isobutyl magnesium bromide (2.0M diethyl ether solution) were added under ice-cooling, and the reaction solution was stirred at the same temperature for 4 hours. To the reaction solution was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))

Sources & evidence

ORD record
ord-eae9981ba4d04ccfaab8bcd1ba53f37f
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

Loading…