Ammonium Chloride → (2,6-Difluoropyridin-4-yl)methanol

HRID 426300Notes

Reaction equation

HRID 426300 reaction equation
C([O:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[N:14]=[C:13]([F:18])[CH:12]=1)(=O)C1C=CC=CC=1.C[O-].[Na+].[Cl-].[NH4+]>CO>[F:18][C:13]1[CH:12]=[C:11]([CH2:10][OH:9])[CH:16]=[C:15]([F:17])[N:14]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 59184643(2,6-Difluoropyridin-4-yl)methyl benzoate

Product 1

HCID 59184676(2,6-Difluoropyridin-4-yl)methanolYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (2,6-difluoropyridin-4-yl)methyl benzoate (10.29 g, 41.325 mmol) in anhydrous methanol (80 mL) at room temperature, was added sodium methoxide (2.23 g, 41.325 mmol). After stirring for 20 min., excess ammonium chloride was added to the reaction mixture and stirring was continued for 30 min. The mixture was then evaporated in vacuo and the residue was dissolved in methanol-MC (1:9), filtered, and the filtrate was evaporated in vacuo to give a crude product. The crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:2 to 2:1)) to afford 5.9 g (98%) of (2,6-difluoropyridin-4-yl)methanol as a white solid. m.p. 66-67° C. 1H NMR (200 MHz, CDCl3) δ 2.19 (1H, t, J=5.8 Hz), 4.81 (2H, d, J=5.8 Hz), 6.84 (2H, s).

Workup

  1. stirringstirring
  2. waitwas continued for 30 min
  3. customThe mixture was then evaporated in vacuo
  4. dissolutionthe residue was dissolved in methanol-MC (1:9)
  5. filtrationfiltered
  6. customthe filtrate was evaporated in vacuo
  7. customto give a crude product
  8. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexane (1:2 to 2:1))

Sources & evidence

ORD record
ord-8a7aa6e4bb15441f82864dac349c7033
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…