Sodium borohydride → (2-Chloro-5-methylpyridin-3-yl)methanol

HRID 413474Notes

Reaction equation

HRID 413474 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([CH:10]=[O:11])=[CH:8][C:7]([CH3:12])=[CH:6][N:5]=1>CO>[Cl:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][C:7]([CH3:12])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 98340182-Chloro-5-methylpyridine-3-carbaldehyde

Product 1

HCID 12056721(2-Chloro-5-methylpyridin-3-yl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.65 g, 0.0167 moles) was added slowly to a well-stirred solution of 2-chloro-5-methylpyridine-3-carbaldehyde (1.3 g, 0.0084 moles) in methanol (20 ml) at 0° C. temperature over a period of 15 minutes. The reaction mass was further stirred for 2 hours at the same temperature. The solvent was removed under reduced pressure and the mass was quenched with water (25 ml). The mass was extracted with ethyl acetate (2×50 ml) and the layers separated. The organic layer was removed under reduced pressure. The residue so obtained was subjected to chromatographic purification on silica gel to give 2-chloro-3-hydroxymethyl-5-methylpyridine as a solid in 88 % yield.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe mass was quenched with water (25 ml)
  3. extractionThe mass was extracted with ethyl acetate (2×50 ml)
  4. customthe layers separated
  5. customThe organic layer was removed under reduced pressure
  6. customThe residue so obtained
  7. customwas subjected to chromatographic purification on silica gel

Sources & evidence

ORD record
ord-55e33fcc56a84aee8883be0977b9913f
Source dataset
uspto-grants-2003_05
Patent number
US06566528B1

Reaction notes

Loading…