Sodium bis(trimethylsilyl)amide → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25790

Reaktionsgleichung

Reaktionsgleichung von HRID 25790
C(OC(N1C2C(=CC(C3C=CC=CC=3OC)=CC=2)C(C(O)C)=CC1(C)C)=O)(C)(C)C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[NH:45][C:44]([CH3:50])([CH3:49])[CH:43]=[C:42]2[CH:51]([O:53][CH2:54][CH:55]=[C:56](C)[CH3:57])[CH3:52].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.BrCC=C(C)C>[CH2:54]([O:53][CH:51]([C:42]1[C:41]2[C:46](=[CH:47][CH:48]=[C:39]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[O:32][CH3:31])[CH:40]=2)[NH:45][C:44]([CH3:50])([CH3:49])[CH:43]=1)[CH3:52])/[CH:55]=[CH:56]/[CH3:57]

Komponenten

5

Edukt 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 691537276-(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

Produkt 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 700922-Butene, 1-bromo-3-methyl-Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customto give the alkylated product, which

Quellen und Nachweise

ORD-Eintrag
ord-d5f249d5ca93471aaf3c153cf810d56a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

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