Water → HCID 20205106, compound

HRID 978108Notes

Reaction equation

HRID 978108 reaction equation
[H-].[CH2:2]1[O:6][C:5]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:4]=2[O:3]1.Cl[CH:13]([C:19]([CH3:21])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].O>CN(C=O)C>[CH2:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH:13]([C:19]([CH3:21])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C:5]=2[O:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 11858Ethyl 2-chloroacetoacetateHCID 68289SesamolHCID 166653Hydride

Product 1

HCID 20205106HCID 20205106, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 1 L DMF, sodiul hydride (8.7 g, 0.36 mole, 1 eq.) was added under N2 at room temperature. Then sesamol (50 g, 0.36 mole) was added portionwise to the reaction mixture and stirred 20 minutes at room temperature. Ethyl 2-chloroacetoacetate (59.6 g, 1 eq.) was added slowly and the mixture was heated to 100° C. using an oil bath for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate, dried over magnesium sulfate and evaporated. The residue was flash chromatographed using hexane ethyl acetate 10%, to give: 50 g (52% yield) of ethyl 2-(3,4-methylenedioxyphenoxy)acetoacetate.

Workup

  1. temperaturethe mixture was heated to 100° C.
  2. customfor 3 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customchromatographed
  7. customto give

Sources & evidence

ORD record
ord-b08cd9fc528e4bc3abe8944b6c7f32cb
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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