Ammonium Chloride → (3,5-Difluoropyridin-2-YL)methanol

HRID 2172637Notes

Reaction equation

HRID 2172637 reaction equation
C([O:3][C:4]([C:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[CH:8][N:7]=1)=O)C.[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[F:12][C:11]1[C:6]([CH2:4][OH:3])=[N:7][CH:8]=[C:9]([F:13])[CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 46311358Ethyl 3,5-difluoropyridine-2-carboxylate

Product 1

HCID 53414314(3,5-Difluoropyridin-2-YL)methanolYield 98.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-difluoro-pyridine-2-carboxylic acid ethyl ester of Step A (2.5 g, 12.6 mmol) in ethanol (10 mL), cooled using an ice water bath, was added sodium borohydride (1.43 g, 37.8 mmol) in a portion wise manner. The solution was stirred at 0° C. for thirty minutes and at ambient temperature for two hours. The reaction was returned to 0° C. and saturated ammonium chloride was added dropwise. The solvent was removed in vacuo and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated ammonium chloride, water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the alcohol as a yellow oil (1.8 g, 98%). MS (M+H): 146

Workup

  1. customwas returned to 0° C.
  2. customThe solvent was removed in vacuo
  3. customthe resulting residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated ammonium chloride, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe slurry was filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-784d3e8868404d2fbf34d29aced4186d
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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