Water → (3,5-Dichloropyridin-4-yl)methanol

HRID 577165Notes

Reaction equation

HRID 577165 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+].O>CO>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 17855219(3,5-Dichloropyridin-4-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 0° C. solution of 3,5-dichloropyridine-4-carbaldehyde (7.0 g, 40 mmol) in anhydrous methanol (500 mL) was added sodium borohydride (2.3 g, 60 mmol). The reaction mixture was stirred at room temperature for 3 hours. Water (150 mL) was added and MeOH was evaporated. The mixture was extracted with ethyl acetate (2×100 mL) and 2-butanol (1×100 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (3,5-dichloropyridin-4-yl)methanol (6.4 g, 90% yield), which was used without further purification.

Workup

  1. customMeOH was evaporated
  2. extractionThe mixture was extracted with ethyl acetate (2×100 mL) and 2-butanol (1×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8626e562765a49c397f169041351b444
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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