Sodium Chloride → Rac-6-methoxy-2-(3-oxo-2-butyl)-1-indanone

HRID 264469

반응식

HRID 264469 반응식
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].[CH3:21][O:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][CH2:28][C:29]2=[O:32])=[CH:25][CH:24]=1.[Cl-].[Na+].[O:35]1CCCC1>CCCCCC>[CH3:21][O:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][CH:28]([CH:17]([C:18](=[O:35])[CH3:19])[CH3:16])[C:29]2=[O:32])=[CH:25][CH:24]=1

참가 물질

8

반응물 6

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3회HCID 3340366-Methoxy-1-IndanoneHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

생성물 1

HCID 53687610Rac-6-methoxy-2-(3-oxo-2-butyl)-1-indanone수율 37%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

A lithium diisopropylamide solution, freshly prepared from 3.12 ml of diisopropylamine and 13.8 ml of 1.6N n-butyllithium in hexane, in 40 ml of anhydrous tetrahydrofuran was added dropwise while stirring to a solution, cooled to -70°, of 2.96 g of 6-methoxy-1-indanone in 300 ml of anhydrous tetrahydrofuran. The mixture was stirred at this temperature for an additional 30 minutes and a solution of 2.03 ml of 3-chloro-2-butenone dissolved in 40 ml of anhydrous tetrahydrofuran was subsequently added dropwise over 10 minutes. The reaction mixture was left to come to room temperature over 30 minutes and was stirred at this temperature for a further 30 minutes. Subsequently, the reaction mixture was poured on to 150 ml of ice, 150 ml of saturated sodium chloride were added and the organic phase was separated. The aqueous phase was extracted once with 400 ml of diethyl ether, the combined organic phases were washed once with 200 ml of saturated sodium chloride solution, dried over magnesium sulfate and concentrated in a vacuum. The red oil obtained was purified by column chromatography on silica gel (hexane/diethyl ether 3:2). In addition to 0.93 g of educt there were obtained 1.56 g (37%) of rac-6-methoxy-2-(3-oxo-2-butyl)-1-indanone as a yellow oil.

후처리

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at this temperature for an additional 30 minutes
  3. additionwas subsequently added dropwise over 10 minutes
  4. waitThe reaction mixture was left
  5. stirringwas stirred at this temperature for a further 30 minutes
  6. additionwere added
  7. customthe organic phase was separated
  8. extractionThe aqueous phase was extracted once with 400 ml of diethyl ether
  9. washthe combined organic phases were washed once with 200 ml of saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in a vacuum
  12. customThe red oil obtained
  13. customwas purified by column chromatography on silica gel (hexane/diethyl ether 3:2)
  14. additionIn addition to 0.93 g of educt

출처 및 근거

ORD 기록
ord-f7f39915f30143158627a1f5c5da9543
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646173

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