Sodium borohydride → (4-Chloro-6-methylpyridin-2-yl)methanol

HRID 2086261Notes

Reaction equation

HRID 2086261 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](OCC)=[O:10])[CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH2:9][OH:10])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22727099Ethyl 4-chloro-6-methylpyridine-2-carboxylate

Product 1

HCID 22727138(4-Chloro-6-methylpyridin-2-yl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 4-chloro-6-methylpyridine-2-carboxylate (0.80 g) in methanol (30 ml) was treated at room temperature portionwise with sodium borohydride (1.51 g) and the reaction mixture was heated under reflux for 2 hours. The reaction mixture was concentrated and the resultant residue was combined with water and ethyl acetate, and the organic phase was isolated, dried and concentrated to obtain the title compound (0.60 g) as a tan powder.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe organic phase was isolated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fbab4c950f7460da320124c38b87706
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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