Benzyl Alcohol → 2-(benzyloxy)isonicotinonitrile

HRID 499313Notes

Reaction equation

HRID 499313 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][N:13]=1.C(OCC)(=O)C>O1CCCC1.O>[CH2:3]([O:10][C:12]1[CH:17]=[C:16]([CH:15]=[CH:14][N:13]=1)[C:18]#[N:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 225035202-(benzyloxy)isonicotinonitrileYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% oil, 0.13 g, 3.3 mmol) was suspended in tetrahydrofuran (2 ml), Benzyl alcohol (0.30 g, 3.2 mmol) was added thereto and the mixture was stirred for 30 minutes. A solution of 2-chloro-4-cyanopyridine (0.40 g, 2.9 mmol) in tetrahydrofuran (1 ml) was added to the mixture and the mixture was refluxed for 6 hrs. The reaction mixture was combined with ethyl acetate and water and stirred. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was subjected to a silica gel (30 g) column chromatography, eluted with hexane-ethyl acetate (4:1, v/v) to give the titled compound (0.37 g, 62%).

Workup

  1. temperaturethe mixture was refluxed for 6 hrs
  2. stirringstirred
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. washeluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record
ord-f06fb8007d9c4b80bbce8810b1fad125
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…