Chloroform → HCID 178466778, compound

HRID 547638Notes

Reaction equation

HRID 547638 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1.C(Cl)(Cl)Cl.NC1C=C(OC2C=CC(C(O)C)=CC=2)C=CC=1N>C(O)C.O=[Mn]=O>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 57585929HCID 57585929, compoundHCID 178466779HCID 178466779, compound

Product 1

HCID 178466778HCID 178466778, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 702EthanolSolvent

Procedure

Crude 1-[4-(1H-benzimidazol-5-yloxy)phenyl]ethanol was dissolved in 75 mL of 1:1 ethanol:chloroform and stirred with MnO2 (1.4 g, 10 equivalents based on step 2 starting material) at 80 degrees Centigrade for approximately 18 hours. A second 1.4 g of MnO2 was added and the reaction was heated for an additional 24 hours. A third 1.4 g of MnO2 was added and the reaction was heated for an additional 24 hours. The reaction was filtered through celite and concentrated onto basic alumina. The crude product was purified by silica gel column chromatography to give 1-[4-(1H-benzimidazol-5-yloxy)phenyl]ethanone and an impurity that was carried forward to the next step. (M+1) 253.0, 1.41 min (LC/MS method B).

Workup

  1. temperaturethe reaction was heated for an additional 24 hours
  2. temperaturethe reaction was heated for an additional 24 hours
  3. filtrationThe reaction was filtered through celite
  4. concentrationconcentrated onto basic alumina
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7b07ed601f70400e95498bdd52acf1a8
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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