Ethanol → Ethyl 5-(hydroxymethyl)pyridine-2-carboxylate

HRID 501818Notes

Reaction equation

HRID 501818 reaction equation
[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].C(O[C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[N:15][CH:16]=1)=[O:10])C.S(=O)(=O)(O)O.[CH2:25](O)[CH3:26]>>[OH:10][CH2:9][C:11]1[CH:12]=[CH:13][C:14]([C:17]([O:19][CH2:25][CH3:26])=[O:18])=[N:15][CH:16]=1

Participants

6

Reactant 5

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 59208717880-34-1HCID 4311764Sodium borohydrideHCID 5284359Calcium Chloride

Product 1

HCID 13518564Ethyl 5-(hydroxymethyl)pyridine-2-carboxylate

Procedure

0.636 g of sodium borohydride was added to 22 mL of ice-cooled ethanol, to which a solution of 1.09 g of calcium chloride in 14 mL of ethanol was added dropwise, followed by addition of 1.20 g of 5-(ethoxycarbonyl)-2-pyridinecarboxylic acid ½ calcium salt, and this mixture was stirred for one hour at room temperature. The reaction mixture, to which 2.8 mL of concentrated sulfuric acid was added, was stirred for 6 hours while heating it under reflux. The reaction mixture was cooled to room temperature and concentrated under reduced pressure followed by successive addition of a saturated aqueous solution of sodium hydrogen carbonate and chloroform, and then the organic phase was separated therefrom. The resultant organic phase was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 0.34 g of ethyl 5-(hydroxymethyl)-2-pyridinecarboxylate as light yellow solid.

Workup

  1. stirringwas stirred for 6 hours
  2. temperaturewhile heating it
  3. temperatureunder reflux
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated under reduced pressure
  6. additionfollowed by successive addition of a saturated aqueous solution of sodium hydrogen carbonate and chloroform
  7. customthe organic phase was separated
  8. washThe resultant organic phase was washed with a saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-8aea6389fda448f4b9bb5069139d32a6
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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