1,2-Cyclooctanedione → (Z)-2-(4,4-dimethyl-2-oxo-pentyl)-cyclooct-2-enone

HRID 1985599Notes

Reaction equation

HRID 1985599 reaction equation
CC(C)([O-])C.[K+].COP([CH2:13][C:14](=[O:20])[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=O)OC.[C:21]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[O:29]>C(O)(C)(C)C>[CH3:19][C:16]([CH3:17])([CH3:18])[CH2:15][C:14](=[O:20])[CH2:13][C:21]1[C:22](=[O:29])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=1

Participants

5

Reactant 3

HCID 5436981,2-CyclooctanedioneHCID 23665647Potassium tert-butoxideHCID 25112585(4,4-Dimethyl-2-oxo-pentyl)-phosphonic acid dimethyl ester

Product 1

HCID 25112586(Z)-2-(4,4-dimethyl-2-oxo-pentyl)-cyclooct-2-enoneYield 22.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of potassium tert-butoxide (0.192 g) in tert-butanol (10 mL) under an argon atmosphere was treated at 50° C. with (4,4-dimethyl-2-oxo-pentyl)-phosphonic acid dimethyl ester (0.38 g) and cyclooctane-1,2-dione (0,2 g), and the mixture was then heated at reflux for 12 h under an argon atmosphere. The reaction mixture was partitioned between water and AcOEt, the layers were separated, the aqueous layer extracted twice with AcOEt. The combined organic layers were washed with water, dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100% to 95%) to give (Z)-2-(4,4-dimethyl-2-oxo-pentyl)-cyclooct-2-enone (0.076 g) as a light yellow oil. MS (ESI): 237.0 (MH+).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 12 h under an argon atmosphere
  3. customThe reaction mixture was partitioned between water and AcOEt
  4. customthe layers were separated
  5. extractionthe aqueous layer extracted twice with AcOEt
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (heptane/AcOEt 100% to 95%)

Sources & evidence

ORD record
ord-0b4ec987d14549c0aa8e927d819d4736
Source dataset
uspto-grants-2009_06
Patent number
US07547697B2

Reaction notes

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