Selenium Dioxide → HCID 23440827, compound

HRID 2304693Notes

Reaction equation

HRID 2304693 reaction equation
[Se](=O)=[O:2].[Br:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=1>O1CCOCC1.O>[Br:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH:15]=[O:2])=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24007Selenium Dioxide2×HCID 234408111-(4-(2-Bromoethoxy)phenyl)ethanone

Product 1

HCID 23440827HCID 23440827, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of selenium dioxide (0.821 g, 7.4 mmol) in 1,4-dioxane (40 mL) and water (3 mL) was heated at 55° C. until selenium dioxide was dissolved. To the solution was added 1-[4-(2-bromoethoxy)phenyl]ethanone (1.80 g, 7.4 mmol), and the reaction was heated to reflux for 4 hours. The reaction was filtered, concentrated, and purified by column chromatography (SiO2, 50% ethyl acetate/hexane) to provide the title compound (1.853 g, 97% yield): ES-MS (m/z) 257 [M+H]+.

Workup

  1. dissolutionwas dissolved
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 4 hours
  4. filtrationThe reaction was filtered
  5. concentrationconcentrated
  6. custompurified by column chromatography (SiO2, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5bc5dc68c5b14d1d93c92b1ff3c68440
Source dataset
uspto-grants-2002_08
Patent number
US06436923B1

Reaction notes

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