Water → (3-Fluoropyridin-4-yl)methanol

HRID 630012

Reaction equation

HRID 630012 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]=[O:11].O>CO>[F:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 27630033-FluoroisonicotinaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 49760376(3-Fluoropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium borohydride (454 mg, 12.0 mmol) in anhydrous methanol (15 mL) was added a solution of 3-fluoropyridine-4-carbaldehyde (1.0 g, 8.0 mmol) in anhydrous methanol (5 mL) at 0° C. The mixture was stirred overnight at room temperature. Water was added and extracted 3 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (3-fluoropyridin-4-yl)methanol was obtained and used in the next step without purification; 1H NMR (400 MHz, CDCl3): δ 2.25 (bs, 1H), 4.85 (d, J=5.7 Hz, 2H), 7.50 (t, J=5.2 Hz, 1H) 8.38-8.43 (m, 2H).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-5df5cd3c29e8482bb8a9ad8af61f4ba8
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Linked notes

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