Hydrochloric Acid → (2-Chloro-6-methylpyridin-4-yl)methanol

HRID 1043909Notes

Reaction equation

HRID 1043909 reaction equation
B.C1COCC1.[Cl:7][C:8]1[CH:13]=[C:12]([C:14](O)=[O:15])[CH:11]=[C:10]([CH3:17])[N:9]=1.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([CH3:17])[N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1412092-Chloro-6-methylpyridine-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-THF complex (16.5 mL, 1.06 M solution in THF) was added to a solution of 2-chloro-6-methylpyridine-4-carboxylic acid (2 g) in THF (10 mL), and the mixture was heated under reflux for 12 hours. 5 M hydrochloric acid was added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was neutralized by adding a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%) to give the title compound (1.75 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%)

Sources & evidence

ORD record
ord-3876828d05634dd6acc8ce403ee9742c
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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