Sodium hydride → Ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionate

HRID 53977

Reaktionsgleichung

Reaktionsgleichung von HRID 53977
[CH2:1]([O:3][C:4]([CH:6]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])[CH3:2].[H-].[Na+].[Br:22][C:23]1[CH:33]=[CH:32][C:26]2[S:27][C:28]([CH2:30]Br)=[CH:29][C:25]=2[CH:24]=1.[Cl-].[NH4+]>O1CCCC1>[Br:22][C:23]1[CH:33]=[CH:32][C:26]2[S:27][C:28]([CH2:30][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])([C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:29][C:25]=2[CH:24]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2785178Diethyl 2-(4-methoxyphenyl)malonateHCID 148193525-Bromo-2-(bromomethyl)benzo[b]thiophene

Produkt 1

HCID 21844202Ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionateAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

14.2 g of ethyl 2-ethoxycarbonyl-2-(4-methoxyphenyl)acetate was dissolved in 150 ml of tetrahydrofuran. 2.6 g of sodium hydride (oil type, 60%) was added to the above solution while stirring under ice cooling, and the stirring was continued for 20 minutes. To this was further added 17.2 g of 5-bromo-2-bromomethylbenzo[b]thiophene. After stirring at room temperature for 18 hours, the resulting reaction solution was mixed with ammonium chloride aqueous solution, and then extracted with ethyl acetate. After drying to distill off the solvent, the resulting residue was subjected to silica gel column chromatography using chloroform as an elution solvent, thereby obtaining 24.2 g of ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionate.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 18 hours
  2. customthe resulting reaction solution
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. distillationto distill off the solvent

Quellen und Nachweise

ORD-Eintrag
ord-dbde7cd1490149faa0abad586b4db122
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620991

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