Diethyl Malonate → Diethyl (6-propyl-1,3-benzodioxole-5-yl)methylmalonate

HRID 1195267

Reaktionsgleichung

Reaktionsgleichung von HRID 1195267
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]1[C:28]([CH2:29][CH2:30][CH3:31])=[CH:27][C:23]2[O:24][CH2:25][O:26][C:22]=2[CH:21]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:29]([C:28]1[C:20]([CH2:19][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:21][C:22]2[O:26][CH2:25][O:24][C:23]=2[CH:27]=1)[CH2:30][CH3:31]

Komponenten

6

Edukt 3

HCID 7761Diethyl MalonateHCID 11430Potassium CarbonateHCID 747395-(Chloromethyl)-6-propyl-1,3-benzodioxole

Produkt 1

HCID 57050645Diethyl (6-propyl-1,3-benzodioxole-5-yl)methylmalonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

24.3 g of diethyl malonate, 42 g of potassium carbonate, 300 ml of acetone and a catalytic amount of tetrabutylammonium bromide were added to 16.1 g of crude 5-chloromethyl-6-propyl-1,3-benzodioxole and the mixture was heated under reflux for 25 h. The reaction mixture was filtered and the residue was washed with acetone. The washing was combined with the filtrate. The solvent was distilled off. 500 ml of ethyl acetate and 500 ml of water were added thereto and the layers thus formed were separated. The ethyl acetate layer was washed with water three times and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 16.5 g of the crude intended compound in the form of a colorless oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 25 h
  3. filtrationThe reaction mixture was filtered
  4. washthe residue was washed with acetone
  5. distillationThe solvent was distilled off
  6. addition500 ml of ethyl acetate and 500 ml of water were added
  7. customthe layers thus formed
  8. customwere separated
  9. washThe ethyl acetate layer was washed with water three times
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled off
  12. customto obtain 16.5 g of the crude intended compound in the form of a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-a814166a4eb94021b564004f2e9e9e7f
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110956

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