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

HRID 1959542Notes

Reaction equation

HRID 1959542 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:12])[C:9]=1[CH:10]=[O:11]>C(O)C>[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:12])[C:9]=1[CH2:10][OH:11]

Participants

4

Reactant 2

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

Product 1

HCID 17855219(3,5-Dichloropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (0.838 g, 22.2 mmol) was added to a stirred solution of 3,5-dichloro-pyridine-4-carbaldehyde (3.0 g, 17 mmol) in ethanol (40 mL). After stirring for 35 min at room temperature, the reaction mixture was concentrated in vacuo, the residue was redissolved in ethyl acetate (200 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS (m/z): 178.1 [M+H+].

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was redissolved in ethyl acetate (200 mL)
  3. washwashed with water (50 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60df8377dd3240d493043d9ef0f738b5
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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