Reaktion #54065

ord-ce9a7ee077a34850b30661c174215de3

Reaktionsgleichung

COc1ccccc1-c1ccc2c(c1)C(C(C)O)=CC(C)(C)N2C(=O)OC(C)(C)C.COc1ccccc1-c1ccc2c(c1)C(C(C)OCCC1CCCCC1)=CC(C)(C)N2

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

sodium bis(trimethylsilyl)amide

2-cyclohexylethyl bromide

→

C/C=C/COC(C)C1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21

title compound

Ausbeute 101.0%

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

Ausbeute 101.0%

Edukte

—

solution

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

sodium bis(trimethylsilyl)amide

2-cyclohexylethyl bromide

Reagenzien

Keine

Lösungsmittel

THF

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
Sonstigeto give the alkylated product, which

Vorschrift

4-[1-(2-Cyclohexylethoxy)ethyl]-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (70 mg) was treated with 255 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 49 mg of 2-cyclohexylethyl bromide to give the alkylated product, which was deprotected to yield 31 mg of title compound as an oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858627B2uspto-grants-2005_02