HCID 21938179, compound → HCID 21937930, compound

HRID 2054614Notes

Reaction equation

HRID 2054614 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][CH2:18][CH2:19][OH:20])[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=[O:29].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[C:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][CH2:18][C:19]([OH:29])=[O:20])[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21938179HCID 21938179, compoundHCID 131709961Jones' reagent

Product 1

HCID 21937930HCID 21937930, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-15 °C

Procedure

100 mg of 3-[(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]propan-1-ol was introduced into 2.5 ml of acetone and mixed at −15° C. with 0.15 ml of a solution of Jones reagent (produced from 0.27 g of chromium(VI) oxide, 1 ml of water and 0.23 ml of concentrated sulfuric acid). After 3.5 hours of stirring at −15° C., it was quenched with the addition of isopropanol. It was diluted with water, extracted three times with dichloromethane, the combined organic phases were dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was purified by chromatography on silica gel.

Workup

  1. customit was quenched with the addition of isopropanol
  2. additionIt was diluted with water
  3. extractionextracted three times with dichloromethane
  4. customthe combined organic phases were dried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a4397f395cf4311a29ae4f2ac11b855
Source dataset
uspto-grants-2008_02
Patent number
US07329679B2

Reaction notes

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