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Sodium hydride → methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate

HRID 1176597
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Reaktionsgleichung

Reaktionsgleichung von HRID 1176597
[O:1]=[C:2]1[NH:8][C:7]2[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:1]=[C:2]1[N:8]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])[C:7]2[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1
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Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 68497596Methyl 2-oxo-2,3,4,5-tetrahydro-1H-benz[b]azepine-9-carboxylate

Produkt 1

HCID 68634682methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2.500 g of methyl 2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate are dissolved under argon in 30 ml of N,N-dimethylformamide and the solution is cooled to 0° C. in an ice bath. 0.600 g of sodium hydride dispersion (60%) is added in portions and the reaction mixture is subsequently stirred at 0° C. over a further 1 hour. 0.502 ml of 2-(trimethylsilyl)ethoxymethyl chloride is added and the reaction mixture is subsequently stirred at room temperature over 11 hours. The reaction mixture is poured onto 150 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with 2×150 ml of tert-butyl methyl ether. The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a reddish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (1:1 EtOAc-heptane); Rt=5.02.

Aufarbeitung

  1. stirringthe reaction mixture is subsequently stirred at room temperature over 11 hours
  2. extractionextracted with 2×150 ml of tert-butyl methyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-e92c9576896a4d9a86eda5158434931e
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842688B2

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