Sodium Chloride → 6-Chloro-5-methyl-2-pyridinemethanol

HRID 376299Notes

Reaction equation

HRID 376299 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([Cl:15])[N:9]=1)=O)C.[Cl-].[Na+]>C(O)C>[Cl:15][C:10]1[N:9]=[C:8]([CH2:6][OH:5])[CH:13]=[CH:12][C:11]=1[CH3:14]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 9837074Ethyl 6-chloro-5-methylpicolinate

Product 1

HCID 104871386-Chloro-5-methyl-2-pyridinemethanolYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.40 g of sodium borohydride (10.5 mmol) is added in portions to a solution of 1.20 g of 6-chloro-5-methylpyridine-2-carboxylic acid ethyl ester (6.00 mmol) and 10 ml of ethanol maintained at room temperature. The mixture is stirred for 4 hours and then the mixture is poured into an aqueous solution of sodium chloride and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: chloroform). 0.69 g of a colorless oil is recovered.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-985e6d9e57ba4ff29986cc6b195b8960
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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