Hydrochloric Acid → (4-Chloro-3,5-dimethylpyridin-2-YL)methanol

HRID 2304812Notes

Reaction equation

HRID 2304812 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([C:9](OCC)=[O:10])[C:3]=1[CH3:14].[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH2:9][OH:10])[C:3]=1[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10220000Ethyl 4-chloro-3,5-dimethylpicolinate

Product 1

HCID 9795246(4-Chloro-3,5-dimethylpyridin-2-YL)methanolYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-2-ethoxycarbonyl-3,5-Lutidine (1 equivalent) was dissolved in methanol (4 volumes). The solution was cooled in an ice bath and while stirring sodium borohydride (1-4 eq.) was added in portions. The mixture was stirred and heated to reflux (80-85ℑC.). At the end of the reaction, the solvent was evaporated, water (2 volumes) was added and the product was extracted with toluene (2×4 volumes). The combined organic layers were stirred in an ice bath and HCl gas (1.2 eq.) was bubbled in solution. The 4-Chloro-2-hydroxymethyl-3,5-Lutidine hydrochloride salt was filtered, washed with toluene and dried at 50ℑ C. at high vacuum. The product was obtained as a white solid in 85% yield.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. additionwas added in portions
  3. temperatureheated
  4. temperatureto reflux (80-85ℑC.)
  5. customAt the end of the reaction
  6. customthe solvent was evaporated
  7. additionwater (2 volumes) was added
  8. extractionthe product was extracted with toluene (2×4 volumes)
  9. stirringThe combined organic layers were stirred in an ice bath
  10. filtrationThe 4-Chloro-2-hydroxymethyl-3,5-Lutidine hydrochloride salt was filtered
  11. washwashed with toluene
  12. customdried at 50ℑ C
  13. customThe product was obtained as a white solid in 85% yield

Sources & evidence

ORD record
ord-4f9692f4ea43487aac351ef286b169a2
Source dataset
uspto-grants-2002_08
Patent number
US06437139B1

Reaction notes

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