Water → 4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25783

Reaktionsgleichung

Reaktionsgleichung von HRID 25783
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH:26]([OH:28])[CH3:27])=[CH:10][C:9]1([CH3:30])[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:41](Br)[CH:42]=[CH:43][CH3:44].O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[CH:15][CH:16]=2)[C:11]([CH:26]([O:28][CH2:41]/[CH:42]=[CH:43]/[CH3:44])[CH3:27])=[CH:10][C:9]1([CH3:29])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1224142-Butene, 1-bromo-HCID 2724254Sodium bis(trimethylsilyl)amideHCID 207603324-(1-hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 207603314-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl esterAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 70 mg of 4-(1-hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester in 2 mL of DMSO was treated with 0.22 mL of 1.0 M sodium bis(trimethylsilyl)amide and 29 mg of crotyl bromide at room temperature. The reaction mixture was allowed to stir at room temperature overnight. The reaction was worked up by adding water and extracted with EtOAc three times. The organic layers were combined, washed sequentially with saturated aqueous sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to yield 58 mg of 4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

Aufarbeitung

  1. extractionextracted with EtOAc three times
  2. washwashed sequentially with saturated aqueous sodium bicarbonate solution, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-98eef52007ea4f0caa6af926eb09b25a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

Verknüpfte Notizen

Wird geladen…