Oxyselenide → (E,E)-11,11-Diethoxy-2,6-dimethyl-10-oxo-2,6-undecadien-1-ol

HRID 443376

Reaction equation

HRID 443376 reaction equation
[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5](=[O:17])[CH2:6][CH2:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:2].[Se]=[O:22]>C(O)C>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:17])[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:16])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:15])/[CH2:14][OH:22])[CH3:20]

Participants

4

Reactant 2

HCID 167175OxyselenideHCID 538849131,1-Diethoxy-6,10-dimethylundeca-5,9-dien-2-one

Product 1

HCID 23466456(E,E)-11,11-Diethoxy-2,6-dimethyl-10-oxo-2,6-undecadien-1-olYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 70 ml of 95% ethanol was dissolved 7.4 g of 1,1-diethoxy-6,10-dimethyl-2-oxo-5,9-undecadien, and the resulting solution was, after addition of 1.7 g of selenium oxide, refluxed for 15 minutes. The ethanol was removed by evaporation, and the residue was, after addition of water, extracted with ether. The ethereal extract was washed with an aqueous sodium hydrogencarbonate solution and dried. The solvent was then removed by evaporation to leave an oil, and the oil was purified by the silica gel column chromatography to yield 3.0 g of the desired product.

Workup

  1. temperaturerefluxed for 15 minutes
  2. customThe ethanol was removed by evaporation
  3. additionafter addition of water
  4. extractionextracted with ether
  5. extractionThe ethereal extract
  6. washwas washed with an aqueous sodium hydrogencarbonate solution
  7. customdried
  8. customThe solvent was then removed by evaporation
  9. customto leave an oil
  10. customthe oil was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-e1ecc981299341cca731e4cb64c5be25
Source dataset
uspto-grants-1981_04
Patent number
US04260551

Linked notes

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