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

HRID 1744228Notes

Reaction equation

HRID 1744228 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), 4.94 (2H, br. s), 2.28 (1H, br. s).

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-8368cf18422141d490745ffeee05bc87
Source dataset
uspto-grants-2006_03
Patent number
US07015216B2

Reaction notes

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