Acrolein → HCID 15463313, compound

HRID 1596384Notes

Reaction equation

HRID 1596384 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]([CH:9]=[CH2:10])=[O:8].[CH:11]([C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][C:25]=1[OH:26])[CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=O>O1CCOCC1>[CH:7]([C:9]1[CH2:10][O:26][C:25]2[CH:24]=[CH:23][C:15]([CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:14][C:13]=2[CH:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 13365754HCID 13365754, compound

Product 1

HCID 15463313HCID 15463313, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2.21 g of potassium carbonate and 2.20 ml of acrolein were added to a solution of 3.50 g (16.4 mmol) of 3-(3′-formyl-4′-hydroxybenzyl)pyridine in 1,4-dioxane (40 ml) and the mixture was heated at 100° C. for 30 minutes. Then, the resultant reaction mixture was filtered by using Celite (Trademark) and the filtrate was evaporated in vacuo. The residue was purified by a silica gel column chromatography (i.e., hexane: ethyl acetate=2:1 to 1:2) to obtain 3.88 g (yield=94.3%) of the desired compound as a yellow crystal.

Workup

  1. customThen, the resultant reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography (i.e., hexane: ethyl acetate=2:1 to 1:2)

Sources & evidence

ORD record
ord-a6418a615a7943ed9742c136567884ba
Source dataset
uspto-grants-2001_09
Patent number
US06291482B1

Reaction notes

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