3-Chloro-4-pyridinecarboxaldehyde → (3-Chloropyridin-4-yl)methanol

HRID 1709948Notes

Reaction equation

HRID 1709948 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 27629953-Chloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 12742466(3-Chloropyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-chloro-4-pyridinecarboxaldehyde (43.80g, 0.310mol) in ethanol (200 ml) was cooled in an ice bath and treated with powdered sodium borohydride (5.85 g, 0.155 mol) added in portions over approximately 2 min. The resulting solution was removed from the ice bath and stirred at ambient temperature. After 1 hr the solution was recooled in an ice bath and treated with acetone (22 ml) to decompose excess borohydride. The solution was again removed from the ice bath and stirred at ambient temperature. After 30 min the reaction solution was evaporated under vacuum to a viscous oil.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionadded in portions over approximately 2 min
  3. customThe resulting solution was removed from the ice bath
  4. additiontreated with acetone (22 ml)
  5. customThe solution was again removed from the ice bath
  6. stirringstirred at ambient temperature
  7. customAfter 30 min the reaction solution was evaporated under vacuum to a viscous oil

Sources & evidence

ORD record
ord-64ad037e6486464b86aa8ebc69940ea2
Source dataset
uspto-grants-1990_08
Patent number
US04952397

Reaction notes

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