Butanedione → HCID 22320020, compound

HRID 497578Notes

Reaction equation

HRID 497578 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[O:3][C:2]1=[O:12])[CH2:9]2.C[C:14](=O)[C:15](=[O:17])C.O=O>C(O)(=O)C>[C:15]([C:6]12[CH2:11][CH:1]3[CH2:9][CH:8]([CH2:10][CH:4]([O:3][C:2]3=[O:12])[CH2:5]1)[CH2:7]2)(=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 650ButanedioneHCID 977OxygenHCID 5567274-Oxatricyclo[4.3.1.13,8]undecan-5-one

Product 1

HCID 22320020HCID 22320020, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

In a flask were placed 3-oxatricyclo[4.3.1.14,8]undecan-2-one (16.6 g, 100 mmol), acetylacetonatocobalt [Co(acac)2] (50 mmol), 2,3-butanedione (600 mmol), and acetic acid (100 g). A condenser and an oxygen balloon were attached to the flask, and the mixture in the flask was vigorously stirred at 80° C. for 4 hours. After the completion of the reaction, the reaction mixture was concentrated, followed by addition of toluene and washing with water. The resulting organic layer was concentrated, the concentrate was subjected to silica gel column chromatography and thereby yielded the title compound 6-acetyl-3-oxatricyclo[4.3.1.14,8]undecan-2-one in a yield of 37%.

Workup

  1. customIn a flask were placed
  2. customAfter the completion of the reaction
  3. concentrationthe reaction mixture was concentrated
  4. additionfollowed by addition of toluene
  5. washwashing with water
  6. concentrationThe resulting organic layer was concentrated

Sources & evidence

ORD record
ord-213326070c114b72a4f86b8e608c703b
Source dataset
uspto-grants-2005_09
Patent number
US06949615B2

Reaction notes

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