3,5-Dichloro-4-pyridinecarboxaldehyde → (3,5-Dichloropyridin-4-yl)methanol

HRID 1267971Notes

Reaction equation

HRID 1267971 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=[O:9].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 17855219(3,5-Dichloropyridin-4-yl)methanolYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,5-dichloropyridine-4-carboxaldehyde (1.34 g, 7.6 mmol) in MeOH (10 ml) was treated with NaBH4 (0.29 g, 7.6 mmol) and stirred at room temperature for 2 h. The reaction was quenched with water (5 ml) and concentrated in vacuo. The residue was partitioned between EtOAc (20 ml) and 10% HCl (10 ml). The aqueous layer was extracted with EtOAc and the combined organic extracts, washed with 10% NaHCO3 solution, dried (MgSO4) and concentrated in vacuo to give the title compound as a white solid (1.05 g, 78%). δH (CDCl3) 8.52 (2H, s, pyr-H), 4.94 (2H, br s, CH2OH) and 2.28 (1H, br s, OH).

Workup

  1. customThe reaction was quenched with water (5 ml)
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between EtOAc (20 ml) and 10% HCl (10 ml)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic extracts, washed with 10% NaHCO3 solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7424404ea4e4025bae9d7dafd3a58ab
Source dataset
uspto-grants-2003_04
Patent number
US06555562B1

Reaction notes

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