Acetic Acid → Spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropane]-2,3-dione

HRID 1888879Notes

Reaction equation

HRID 1888879 reaction equation
[C:1]12([CH:7]3[CH2:8][CH2:9][CH:4]1[C:5](=[O:10])[CH2:6]3)[CH2:3][CH2:2]2.C(O)(=[O:13])C>>[C:1]12([CH:4]3[CH2:9][CH2:8][CH:7]1[C:6](=[O:13])[C:5]3=[O:10])[CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 15761091Spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropane]-6-one

Product 1

HCID 144441Spiro[bicyclo[2.2.1]heptane-7,1'-cyclopropane]-2,3-dione

Procedure

A solution of spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropan]-2-one (rac), 8.6 g (synthesis: N. J. Turro, JACS, 1980, 102, 6056) in acetic acid, 38 ml, was treated at RT with SeO2 (16.15 g) and the suspension was then heated at reflux for 12 h. The reaction mixture was cooled to RT, filtered and the filter cake was washed with ethyl acetate. The filtrate was made basic with 3N aqueous NaOH and more AcOEt was added. The layers were separated, the organic layer was dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt: 100% to 90%) to give spiro[bicyclo[2.2.1]heptane-7,1′-cyclopropane]-2,3-dione, (2.5 g) as a yellow solid. MS (ESI): 168 (M+NH4)+.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureat reflux for 12 h
  3. filtrationfiltered
  4. washthe filter cake was washed with ethyl acetate
  5. additionwas added
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography (heptane/AcOEt: 100% to 90%)

Sources & evidence

ORD record
ord-172c05a419c64b21a03e9ea73ffcef72
Source dataset
uspto-grants-2013_08
Patent number
US08501940B2

Reaction notes

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