Reaktion #54068

ord-d5f249d5ca93471aaf3c153cf810d56a

Reaktionsgleichung

COc1ccccc1-c1ccc2c(c1)C(C(C)O)=CC(C)(C)N2C(=O)OC(C)(C)C.COc1ccccc1-c1ccc2c(c1)C(C(C)OCC=C(C)C)=CC(C)(C)N2
6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium bis(trimethylsilyl)amide
→
C/C=C/COC(C)C1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21
title compound
Ausbeute 32.7%
C/C=C/COC(C)C1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21
4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline
Ausbeute 32.7%

Edukte

—
solution
COc1ccccc1-c1ccc2c(c1)C(C(C)O)=CC(C)(C)N2C(=O)OC(C)(C)C.COc1ccccc1-c1ccc2c(c1)C(C(C)OCC=C(C)C)=CC(C)(C)N2
6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium bis(trimethylsilyl)amide

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
CC(C)=CCBr
4-bromo-2-methyl-2-butene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto give the alkylated product, which

Vorschrift

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (96 mg) was treated with 450 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 50 μL of 4-bromo-2-methyl-2-butene to give the alkylated product, which was deprotected to yield 14.5 mg of the title compound as an oil.

Quelle

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