Sodium borohydride → (3-Fluoropyridin-2-yl)methanol

HRID 2257816Notes

Reaction equation

HRID 2257816 reaction equation
[CH:1]([C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 113440173-Fluoro-2-pyridinecarboxaldehyde

Product 1

HCID 19703803(3-Fluoropyridin-2-yl)methanolYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-formyl-3-fluoropyridine (4.0 g, 32 mmol) and sodium borohydride (309 mg, 8 mmol) in absolute ethanol (40 mL) was stirred at 0° C. for 15 minutes and at room temperature for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (5 mL) and filtered through diatomaceous earth to remove solids. The filtrate was evaporated and the resultant white solid was dissolved in ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (5×30 mL) and the combined extracts were dried over anhydrous sodium sulfate. Solvent removal provided 3.78 g (93%) of the titled product as a pale yellow oil:

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride (5 mL)
  2. filtrationfiltered through diatomaceous earth
  3. customto remove solids
  4. customThe filtrate was evaporated
  5. dissolutionthe resultant white solid was dissolved in ethyl acetate
  6. extractionThe aqueous layer was extracted with ethyl acetate (5×30 mL)
  7. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  8. customSolvent removal

Sources & evidence

ORD record
ord-5fdcdfe6e3c841b189025ca4750b8f1b
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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