Ethyl Acetate → HCID 68407746, Verbindung

HRID 73583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73583
[CH3:1][CH:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:5]C=C1.C1C(=O)N([Br:24])C(=O)C1.C([O:28][CH2:29][CH3:30])(=O)C>C1COCC1.O>[Br:24][CH:30]1[CH:29]([OH:28])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:7][CH:2]1[CH3:1]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 59226560HCID 59226560, Verbindung

Produkt 1

HCID 68407746HCID 68407746, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine (1.0 equiv.) in THF and water (1:1, 0.13M) was added NBS (1.5 equiv.) and the reaction was stirred at room temperature for 30 min. Upon completion, ethyl acetate and water were added to the reaction, the organic phase was dried with brine, then sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol as a yellow oil in 80% yield. LC/MS=315.0/313.0 (M+H), LC=2.966 min.

Aufarbeitung

  1. dry with materialthe organic phase was dried with brine
  2. filtrationsodium sulfate, filtered
  3. concentrationconcentrated
  4. customThe crude material was purified via silica gel column chromatography
  5. washeluting with ethyl acetate and hexanes (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-00c9eeef8f5b4a15b15f5de27ac363e7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829193B2

Notizen zur Reaktion

Wird geladen…