Ammonium Chloride → 5-Fluoro-3-pyridinemethanol

HRID 576981Notes

Reaction equation

HRID 576981 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 141411595-Fluoropyridine-3-carbaldehyde

Product 1

HCID 1524495-Fluoro-3-pyridinemethanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 5-fluoropyridine-3-carbaldehyde (500 mg, 4.0 mmol) in anhydrous methanol (20 mL) was added sodium borohydride (150 mg, 4.0 mmol). The reaction mixture was stirred at room temperature for 3 hours. Saturated ammonium chloride solution (20 mL) was added. The resultant mixture was extracted with EtOAc (3×20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (5-fluoropyridin-3-yl)methanol (430 mg, 85% yield). The product was used without further purification.

Workup

  1. extractionThe resultant mixture was extracted with EtOAc (3×20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-37fe8193297a419a9e30d02c2a1811a2
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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