Salicylaldehyde → Ethyl 3-(1-benzofuran-2-yl)-3-oxopropanoate

HRID 429334Notes

Reaction equation

HRID 429334 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[CH2:23]([O:22][C:20]([CH2:19][C:18]([C:17]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=1)=[O:25])=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 12777066Ethyl 3-(1-benzofuran-2-yl)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

122 g of salicylaldehyde 1 and 350 g of potassium carbonate are dissolved in 2L of acetone. While stirring at room temperature, add slowly 165 g of ethyl 4-chloroacetoacetate 2 over a period of 2 hours. When addition is over, stir at reflux for another 4 hours. Cool to room temperature and filter. Wash the filtration cake with 0.5L of acetone. Evaporate the solvent.

Workup

  1. additionWhen addition
  2. stirringstir
  3. temperatureat reflux for another 4 hours
  4. temperatureCool to room temperature
  5. filtrationfilter
  6. washWash the filtration cake with 0.5L of acetone
  7. customEvaporate the solvent

Sources & evidence

ORD record
ord-11ea5f792bcf4826bf05acdc88e89b0c
Source dataset
uspto-grants-2001_11
Patent number
US06316487B1

Reaction notes

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