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Sodium hydride → Ethyl 3-(2-bromo-3,4,5,6-tetramethoxyphenyl)-2-ethoxycarbonyl-2-[3-(4-ethoxycarbonylphenoxy)propyl]propionate

HRID 2268484
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2268484
[CH2:1]([O:3][C:4]([CH:6]([CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].[H-].[Na+].[Br:29][C:30]1[C:35]([CH2:36]Br)=[C:34]([O:38][CH3:39])[C:33]([O:40][CH3:41])=[C:32]([O:42][CH3:43])[C:31]=1[O:44][CH3:45]>CN(C=O)C.O>[Br:29][C:30]1[C:31]([O:44][CH3:45])=[C:32]([O:42][CH3:43])[C:33]([O:40][CH3:41])=[C:34]([O:38][CH3:39])[C:35]=1[CH2:36][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:21]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 18348516Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoateHCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene

Produkt 1

HCID 18348578Ethyl 3-(2-bromo-3,4,5,6-tetramethoxyphenyl)-2-ethoxycarbonyl-2-[3-(4-ethoxycarbonylphenoxy)propyl]propionateAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoate (25.9 g) in DMF (200 ml) was portionwise added sodium hydride (60% oil dispersion, 3.11 g) with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 30 min. To the reaction mixture was dropwise added a solution of 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (28.8 g) in DMF (50 ml) with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 6 hr. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=7:1) to yield the entitled compound (42.6 g) as an oil.

Aufarbeitung

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. temperatureto warm to room temperature
  4. stirringstirred for 6 hr
  5. extractionextracted with diethyl ether
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. customdried
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ba8861c6fef4141be1bde60624f5c67
Quelldatensatz
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06326369B1

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