2,2-Dimethyl-1,3-dioxane-4,6-dione → 1,1-Dimethylethyl β-oxocyclobutanepropanoate

HRID 1449501Notes

Reaction equation

HRID 1449501 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.[C:11](Cl)(O)=O.[CH2:15]1[CH2:18][CH2:17][CH2:16]1>ClCCl.N1C=CC=CC=1>[CH:15]1([C:4](=[O:5])[CH2:6][C:7]([O:9][C:2]([CH3:1])([CH3:10])[CH3:11])=[O:8])[CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 19978106HCID 19978106, compound

Product 1

HCID 538118991,1-Dimethylethyl β-oxocyclobutanepropanoateYield 53.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a mixture of 100 ml of dichloromethane and 15 ml of pyridine was dissolved 12.2 g of meldrum's acid. Under cooling with ice, 10.0 g of cyclobutane carboxychloride was added dropwise to the solution, followed by stirring under room temperature for 2 hours. The solvent was removed under reduced pressure and to the residue was added water. The mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was dissolved in 100 ml of tert-butanol and the solution was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was subjected to column chromatography using 100 g of silica gel. The oily titled compound (7.8 g) was obtained from a chloroform eluate fraction.

Workup

  1. additionwas added dropwise to the solution
  2. customThe solvent was removed under reduced pressure and to the residue
  3. additionwas added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. dissolutionThe residue was dissolved in 100 ml of tert-butanol
  9. temperaturethe solution was heated
  10. temperatureunder reflux for 5 hours
  11. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b8299714164d4789a543b1155c69afe0
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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