Triethylamine → Bicyclo(3.2.1)octane-2,4-dione

HRID 1072773Notes

Reaction equation

HRID 1072773 reaction equation
[CH2:1]=[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[O:3]1.C(N(CC)CC)C.[C-]#N.[K+]>C(#N)C.O>[CH:8]12[CH2:9][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:1][C:2]2=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 129939774-Methylene-3-oxabicyclo[3.2.1]octan-2-one

Product 1

HCID 144686Bicyclo(3.2.1)octane-2,4-dioneYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Analogously to Example P3, 2.76 g (20 mmol) of 4-methylene-3-oxabicyclo[3.2.1]octan-2-one are stirred for 15 hours at room temperature in the presence of 2.23 g (22 mmol) of triethylamine and 0.13 g (2 mmol) of potassium cyanide in 10 ml of acetonitrile. The mixture is heated at 55° for a further 30 minutes and then taken up in water and the neutral components are removed at pH 10 using ethyl acetate. The aqueous phase, acidified to pH 2, is extracted with ethyl acetate, dried over sodium sulfate and concentrated by evaporation, yielding 2.05 g (74.3%0) of pure bicyclo[3.2.1]octane-2,4-dione having a melting point of 129-130° C.

Workup

  1. temperatureThe mixture is heated at 55° for a further 30 minutes
  2. customthe neutral components are removed at pH 10
  3. extractionis extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c15c20d5cf604310935e9c12c4fa718f
Source dataset
uspto-grants-2005_06
Patent number
US06911547B1

Reaction notes

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