1-Bromo-2-methylpropane → 2-Isobutyl-3-ketoglutarate diethyl ester

HRID 2108274

반응식

HRID 2108274 반응식
[O:1]=[C:2]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-]CC.[Mg+2].[O-]CC.Br[CH2:23][CH:24]([CH3:26])[CH3:25]>>[CH3:23][CH:24]([CH3:26])[CH2:25][CH:9]([C:2](=[O:1])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

참가 물질

4

반응물 3

HCID 65551-Bromo-2-methylpropane2회HCID 66045Diethyl acetonedicarboxylateHCID 164963Magnesium ethanolate

생성물 1

HCID 99926592-Isobutyl-3-ketoglutarate diethyl ester수율 62%

실험 절차

Diethyl 3-oxopentanedioate (45.5 ml, 0.25 mol) was added to a suspension of magnesium ethoxide (prepared from magnesium turnings (9 g, 0.375 mol) and iodine (0.1 g) in dry ethanol (275 ml)), and the mixture was heated under reflux for 90 min. 1-Bromo-2-methylpropane (54 ml, 0.5 mol) was added, and the reaction was heated under reflux for 16 h. Further 1-bromo-2-methylpropane (27 ml, 0.25 mol) was added to the boiling mixture, and after 3 h the solvent was evaporated in vacuo. The residue was partitioned between 2N hydrochloric acid and ether. After extracting the aqueous phase with ether, the combined organics were washed successively with water, 5% sodium bicarbonate, water and brine, then were dried (Na2SO4) and evaporated in vacuo. The residue was distilled to give the title compound as a colourless oil (40 g, 62%), bp 118°-120° C. (1mmHg).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 90 min
  3. temperaturethe reaction was heated
  4. temperatureunder reflux for 16 h
  5. customafter 3 h the solvent was evaporated in vacuo
  6. customThe residue was partitioned between 2N hydrochloric acid and ether
  7. extractionAfter extracting the aqueous phase with ether
  8. washthe combined organics were washed successively with water, 5% sodium bicarbonate, water and brine
  9. dry with materialwere dried (Na2SO4)
  10. customevaporated in vacuo
  11. distillationThe residue was distilled

출처 및 근거

ORD 기록
ord-1bb946fc6b95473198e619a0f0a889e5
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937243

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