Acetone → 2-Methoxycarbonyl-5-(2-methyldioxolan-2-yl)-6-oxabicyclo[3,2,1]octan-7-one

HRID 2165443노트

반응식

HRID 2165443 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][C:8](=[CH:11][CH3:12])[CH2:7][CH:6]1[C:13]([O:15]C)=[O:14])=[O:4].[Mn]([O-])(=O)(=O)=[O:18].[K+].C[C:24]([CH3:26])=[O:25]>C(O)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][C:8]2([C:11]3([CH3:12])[O:18][CH2:26][CH2:24][O:25]3)[CH2:7][CH:6]1[C:13](=[O:14])[O:15]2)=[O:4]

참가 물질

5

반응물 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 540253811,2-Di-(methoxycarbonyl)-4-ethylidene-cyclohexane

생성물 1

HCID 134534872-Methoxycarbonyl-5-(2-methyldioxolan-2-yl)-6-oxabicyclo[3,2,1]octan-7-one수율 33%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

8 g of 1,2-di-(methoxycarbonyl)-4-ethylidene-cyclohexane, prepared as described in Example 2, was dissolved in aqueous acetone containing 4.8 ml of acetic acid. An aqueous solution of potassium permanganate was added, and the mixture was allowed to stand for 60 minutes at room temperature. The excess oxidant was then destroyed and the reaction mixture, diluted with water, was extracted with ethyl acetate. The organic phase, washed with water and dried over anhydrous sodium sulphate, was evaporated to dryness under vacuum. The residue (9 g) was dissolved in benzene and refluxed for 60 minutes in the presence of a catalytic amount of p-toluenesulphonic acid. 4 ml of ethylene glycol was added and the reaction mixture was refluxed for a further 2 hours. After conventional work-up, the residue, obtained by evaporating off the solvent, was purified by chromatography on a column of silica gel using as eluent a toluene:acetone mixture (15:1 by volume). 3.0 g of the title compound was isolated (yield 33%): m.p. 69°°-71° C; m/z 271 (MH+). IR (KBr): 1790 cm-1 (C=O five membered ring lactone) 1735 cm -1 (C=O ester); 1720 cm-1 (C=O ketone)

후처리

  1. customThe excess oxidant was then destroyed
  2. additionthe reaction mixture, diluted with water
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase, washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customwas evaporated to dryness under vacuum
  7. dissolutionThe residue (9 g) was dissolved in benzene
  8. temperaturerefluxed for 60 minutes in the presence of a catalytic amount of p-toluenesulphonic acid
  9. addition4 ml of ethylene glycol was added
  10. temperaturethe reaction mixture was refluxed for a further 2 hours
  11. customAfter conventional work-up, the residue, obtained
  12. customby evaporating off the solvent
  13. customwas purified by chromatography on a column of silica gel using as eluent a toluene

출처 및 근거

ORD 기록
ord-ff28c2ad29a8437a8d990d1ce1ed359f
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04939282

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