Dimethylformamide → Ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionate

HRID 2268455

Reaktionsgleichung

Reaktionsgleichung von HRID 2268455
CN(C=O)C.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:31][C:32]1[C:37]([CH2:38]Br)=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([CH2:38][C:37]2[C:32]([Br:31])=[C:33]([O:46][CH3:47])[C:34]([O:44][CH3:45])=[C:35]([O:42][CH3:43])[C:36]=2[O:40][CH3:41])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2823246Diethyl 2-(4-(benzyloxy)phenyl)malonateHCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene2×

Produkt 1

HCID 18348651Ethyl 2-(4-benzyloxyphenyl)-3-(6-bromo-2,3,4,5-tetramethoxyphenyl)-2-ethoxycarbonylpropionateAusbeute 49,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A DMF (120 ml) suspension of ethyl 2-(4-benzyloxyphenyl)-2-ethoxycarbonylacetate (12.0 g, 35.1 mmols), 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (16.9 g, 45.6 mmols) and potassium carbonate (14.5 g, 105 mmols) was stirred at room temperature for 6 hours, and then 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (2.60 g, 7.02 mmols) was added thereto stirring was continued at room temperature for further 6 hours. Water was added to the reaction mixture, which was then extracted with diethyl ether. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (11.0 g) as crystals.

Aufarbeitung

  1. stirringthereto stirring
  2. waitwas continued at room temperature for further 6 hours
  3. extractionwas then extracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried
  6. customThe solvent was evaporated out in vacuo
  7. customthe resulting crude product was purified by recrystallization (from hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-84c101868c234a6ea17a0a5ae58899ec
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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