Hydrochloric Acid → Ethyl 4-(hydroxymethyl)picolinate

HRID 1164883Notes

Reaction equation

HRID 1164883 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]#N)[CH:11]=1)(C(C)(C)C)(C)C.[Na].Cl.[OH-].[Na+].C(=O)([O-])[O-:23].[Na+].[Na+].[CH2:28]([OH:30])[CH3:29]>>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([O:30][CH2:28][CH3:29])=[O:23])[CH:11]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 145414484-(Tert-butyldimethylsilyloxymethyl)pyridinecarbonitrile

Product 1

HCID 14541449Ethyl 4-(hydroxymethyl)picolinate

Procedure

A solution of 21.7 g of 4-(tert-butyl-dimethylsilyloxymethyl)-2-cyanopyridine in 220 ml anhydrous ethanol containing 0.2 g of sodium is stirred at room temperature for 18 hours, cooled to 0° and 22 ml 6N hydrochloric acid is then added. The solution is stirred at room temperature for 18 hours cooled to 0°, 7.5 ml 6N sodium hydroxide added followed by 20 ml saturated aqueous sodium carbonate. Extraction with methylene chloride, then drying, filtering and concentrating the extract yields an oil which crystallizes from ether to yield ethyl 4-(hydroxymethyl)-pyridine-2-carboxylate.

Workup

  1. temperaturecooled to 0°
  2. temperaturecooled to 0°
  3. extractionExtraction with methylene chloride
  4. customdrying
  5. filtrationfiltering
  6. concentrationconcentrating the extract
  7. customyields an oil which
  8. customcrystallizes from ether

Sources & evidence

ORD record
ord-0c13b193caad4a77a59fcefc20a5aa9b
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

Loading…