Triethylamine → HCID 58909965, Verbindung

HRID 1295948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295948
C(N(CC)CC)C.[C:8]([C:12]1[CH:13]=[C:14]([C:23](=[O:25])[CH3:24])[CH:15]=[C:16]([N:20]([CH3:22])[CH3:21])[C:17]=1[O:18][CH3:19])([CH3:11])([CH3:10])[CH3:9].[Br:26]N1C(=O)CCC1=O.C(OCC)(=O)C>O1CCCC1>[Br:26][CH2:24][C:23]([C:14]1[CH:15]=[C:16]([N:20]([CH3:22])[CH3:21])[C:17]([O:18][CH3:19])=[C:12]([C:8]([CH3:11])([CH3:9])[CH3:10])[CH:13]=1)=[O:25]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 589100481-[3-(tert-Butyl)-5-(dimethylamino)-4-methoxyphenyl]-1-ethanone

Produkt 1

HCID 58909965HCID 58909965, VerbindungAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (3.2 ml, 22.9 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (3.02 g, 11.4 mmol) were added to a solution of 1-[3-(tert-butyl)-5-(dimethylamino)-4-methoxyphenyl]-1-ethanone (1.9 g, 7.63 mmol) in tetrahydrofuran (50 ml) while cooling on ice and the mixture was stirred at the same temperature for 30 minutes, after which N-bromosuccinimide (2.7 g, 15.2 mmol) was added and stirring was continued for 30 minutes. Ethyl acetate was added, the reaction mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (2.2 g) as a white solid.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. washthe reaction mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f44c6e2377a94d4683ea4fee1cac7163
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244730B2

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