Benzyl Bromide → HCID 71079101, Verbindung

HRID 2190252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190252
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][CH:13]=[C:14]4[C@@H:19]5[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH2:23][C@:18]5([C:26]([OH:28])=[O:27])[CH2:17][CH2:16][C@@:15]4([CH3:29])[C@:10]3([CH3:30])[CH2:9][CH2:8][C@H:7]1[C:6]([CH3:32])([CH3:31])[C@@H:5]([OH:33])[CH2:4][CH2:3]2.[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:33][C@H:5]1[CH2:4][CH2:3][C@@:2]2([CH3:1])[CH:7]([CH2:8][CH2:9][C@:10]3([CH3:30])[CH:11]2[CH2:12][CH:13]=[C:14]2[C@@:15]3([CH3:29])[CH2:16][CH2:17][C@:18]3([C:26]([O:28][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:27])[CH:19]2[CH2:20][C:21]([CH3:24])([CH3:25])[CH2:22][CH2:23]3)[C:6]1([CH3:32])[CH3:31]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10494Oleanolic AcidHCID 11430Potassium Carbonate

Produkt 1

HCID 71079101HCID 71079101, VerbindungAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of oleanolic acid (1a, 6.0 g, 13.1 mmol), benzyl bromide (2.8 g, 16.4 mmol), K2CO3 (2.7 g, 19.7 mmol) and DMF (120 mL) was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica, 30% EtOAc in hexanes) to provide the sub-title compound (6.6 g, 92%) as a white solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (silica, 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d022033b10504ea1bcab5c85ca773da3
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324264B1

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