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

HRID 1449501노트

반응식

HRID 1449501 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 538118991,1-Dimethylethyl β-oxocyclobutanepropanoate수율 53.7%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b8299714164d4789a543b1155c69afe0
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599813

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