Hydrochloric Acid → Ethyl 4-(hydroxymethyl)picolinate

HRID 345349Notes

Reaction equation

HRID 345349 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-856706da1eb6485792316329bb296762
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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