Sodium borohydride → 2-Fluoro-3-(hydroxymethyl)pyridine

HRID 594967Notes

Reaction equation

HRID 594967 reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 114349442-Fluoropyridine-3-carbaldehyde

Product 1

HCID 147614612-Fluoro-3-(hydroxymethyl)pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-fluoropyridine-3-carboxaldehyde (400 mg, 3.2 mmol) and sodium borohydride (121 mg, 3.2 mmol) in methanol (8 mL) was stirred at rt for 16 h. The mixture was then diluted with EtOAc and washed with H2O, then brine. The organic phase was collected, dried (MgSO4) and concentrated in vacuo to give (2-fluoropyridin-3-yl)methanol.

Workup

  1. washwashed with H2O
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82bb49d257294d05ab2f97295f7c1860
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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