Sulfuric Acid → 6-Methyl-2-pyridylmethanol

HRID 1761404Notes

Reaction equation

HRID 1761404 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].S(=O)(=O)(O)O>CO>[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 707366-Methyl-2-pyridylmethanolYield 6,126.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Methylpyridine-2-carboxaldehyde (0.44 mmole) in 50 ml methanol was reduced with 20.6 mmole sodium borohydride at 0°-5° C. After reduction was complete, the mixture was neutralized (pH 7.5) with 2N sulfuric acid, filtered, the filtrate concentrated and partitioned between chloroform and water. Evaporation of solvent from the organic layer gave 3.32 g of red-black oil which was used in the next step.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. custompartitioned between chloroform and water
  4. customEvaporation of solvent from the organic layer

Sources & evidence

ORD record
ord-ab3bbba856c345069f75850f6aa3ab0c
Source dataset
uspto-grants-1989_05
Patent number
US04826833

Reaction notes

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