Reaktion #54063

Reaktionsgleichung

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-phenylpropoxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

sodium bis(trimethylsilyl)amide

→

title compound

Ausbeute 61.5%

4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline

Ausbeute 61.5%

Lösungsmittel

DMSO

THF

1-bromo-3-phenylpropane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give the alkylated product, which

Vorschrift

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-phenylpropoxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (116 mg) in 2 mL of DMSO was treated with 334 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 52 μL of 1-bromo-3-phenylpropane to give the alkylated product, which was then deprotected (as above) to yield 31 mg of the title compound as an oil.

Quelle