Benzyl Bromide → HCID 71079101, compound

HRID 2190252Notes

Reaction equation

HRID 2190252 reaction equation
[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]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10494Oleanolic AcidHCID 11430Potassium Carbonate

Product 1

HCID 71079101HCID 71079101, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d022033b10504ea1bcab5c85ca773da3
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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