Carbon Dioxide → HCID 20264022, compound

HRID 461065Notes

Reaction equation

HRID 461065 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[CH3:12][C:13]1[C:18]([OH:19])=[C:17]([C:20](OC)=[O:21])[C:16]([C:24](OC)=[O:25])=[C:15]([CH:28]=[CH2:29])[N:14]=1.C(=O)=O>O>[CH3:12][C:13]1[C:18]([OH:19])=[C:17]([CH2:20][OH:21])[C:16]([CH2:24][OH:25])=[C:15]([CH:28]=[CH2:29])[N:14]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl Ether2×HCID 20263984Dimethyl 2-methyl-3-hydroxy-6-vinylpyridine 4,5-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 20264022HCID 20264022, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.15 moles of lithium aluminum hydride in 250 ml. of ether is added dropwise with stirring a solution of 0.05 moles of dimethyl 2-methyl-3-hydroxy-6-vinylpyridine 4,5-dicarboxylate in 150 ml. of ether. The mixture is refluxed for 6 hours and stirred overnight at room temperature. The reaction mixture is cooled and 100 ml. of water added dropwise with stirring. The resulting mixture is saturated with carbon dioxide for 30 minutes and then filtered. The precipitate is stirred with 250 ml. of ethanol-water (1:1) and saturated again with carbon dioxide and filtered. The solid is then extracted twice with 100 ml. of boiling ethanol. The combined filtrates are evaporated to dryness in vacuo. The residue is extracted 5 times with 100 ml. of boiling ethanol. The combined extracts are filtered and evaporated to dryness to give 2-methyl-3-hydroxy-4,5-di(hydroxymethyl)-6-vinylpyridine.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. temperatureThe reaction mixture is cooled
  3. stirringwith stirring
  4. filtrationfiltered
  5. stirringThe precipitate is stirred with 250 ml
  6. filtrationof ethanol-water (1:1) and saturated again with carbon dioxide and filtered
  7. extractionThe solid is then extracted twice with 100 ml
  8. customThe combined filtrates are evaporated to dryness in vacuo
  9. extractionThe residue is extracted 5 times with 100 ml
  10. filtrationThe combined extracts are filtered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-60ae2dc6fe004a40975dcd8b406e22a3
Source dataset
uspto-grants-1977_12
Patent number
US04061759

Reaction notes

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