Sodium ethoxide → HCID 56979888, compound

HRID 1195271Notes

Reaction equation

HRID 1195271 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1.CC[O-].[Na+]>C(O)C>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][CH:13]1[C:5]2[CH:6]=[C:7]3[O:11][CH2:10][O:9][C:8]3=[CH:12][C:4]=2[CH2:3][CH2:2][O:1]1)[CH3:19]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 53998371HCID 53998371, compound

Product 1

HCID 56979888HCID 56979888, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.3 g of ethyl 3-{6-(2-hydroxyethyl)-1,3-benzodioxol-5-yl}acrylate was dissolved in 30 ml of ethanol. A catalytic amount of sodium ethylate was added to the solution and the mixture was heated under reflux for 2 h. The solvent was distilled off and 1N hydrochloric acid and water were added to the residue. After extraction with ethyl acetate followed by washing with a saturated aqueous common salt solution and drying over anhydrous magnesium sulfate, the solvent was distilled off. The residue was purified according to silica gel column chromatography (hexane/ethyl acetate=85:15) to obtain 0.78 g of the intended compound in the form of a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. distillationThe solvent was distilled off
  4. addition1N hydrochloric acid and water were added to the residue
  5. extractionAfter extraction with ethyl acetate
  6. washby washing with a saturated aqueous common salt solution
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified

Sources & evidence

ORD record
ord-5266ba0c3ec74f6e95ccf94ec2b99092
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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