tert-Butoxy bis(dimethylamino)methane → (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one

HRID 1751400Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1751400
C(O[CH:6]([N:10]([CH3:12])[CH3:11])N(C)C)(C)(C)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[C:16]([OH:23])[CH:15]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])/[CH:21]=[CH:6]/[N:10]([CH3:11])[CH3:12])=[C:16]([OH:23])[CH:15]=1

Komponenten

4

Edukt 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Produkt 1

HCID 11737295(E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-oneAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1-tert-Butoxy-N,N,N′,N′-tetramethylmethanediamine (19.2 mL, 93.0 mmol) and solution of 1-(4-bromo-2-hydroxyphenyl)ethanone (10 g, 46.5 mmol) in toluene (100 mL) was heated at 35° C. for 16 hours and at 80° C. for 1 hour. The solvent was removed under reduced pressure. The resulting solid was subjected to flash chromatography with eluant of dichloromethane. The product containing fractions were combined and the solvent was removed under reduced pressure to provide (E)-1-(4-bromo-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one (10.4 g, 38.5 mmol, 82%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe product containing fractions
  3. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-239362f861f843d697b25c49b54be952
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156823B2

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