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Tetrahydrofuran → 7,8-Dimethyl-4,4a,5,6-tetrahydro-2(3H)-naphthalenone

HRID 478071
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인쇄 미리보기

반응식

HRID 478071 반응식
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].C[C:10]1[C:11](=[O:17])[CH2:12][CH2:13][CH2:14][C:15]=1[CH3:16].[CH2:18]1COC[CH2:19]1>>[CH3:18][C:19]1[CH2:16][CH2:15][CH:14]2[C:7]([C:5]=1[CH3:6])=[CH:10][C:11](=[O:17])[CH2:12][CH2:13]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 3

HCID 8028Tetrahydrofuran2회HCID 2724682Lithium diisopropylamideHCID 108878982,3-Dimethyl-2-cyclohexen-1-one

생성물 1

HCID 124539797,8-Dimethyl-4,4a,5,6-tetrahydro-2(3H)-naphthalenone수율 60%

반응 조건

온도
25 °C

실험 절차

To a stirred solution of lithium diisopropylamide (LDA) (22 mmol) in THF (200 ml) at -78° C. was added a solution of 2,3-dimethylcyclohexenone (2.48 g, 20 mmol) in THF (50 ml). The mixture was warmed to 25° C., and the solvent and the amine were removed under vacuum. The resulting solid was dissolved in THF (400 ml) and the solution cooled to -78° C. To this solution was added MVK (1.8 ml, 22 mmol) in THF (100 ml) over 10 min. The resulting mixture was stirred 12 hr at room temperature, then worked up. Removal of solvent yielded the dione as a yellow oil (2.8 g, 60%).

후처리

  1. customthe solvent and the amine were removed under vacuum
  2. dissolutionThe resulting solid was dissolved in THF (400 ml)
  3. temperaturethe solution cooled to -78° C
  4. additionTo this solution was added MVK (1.8 ml, 22 mmol) in THF (100 ml) over 10 min
  5. customRemoval of solvent

출처 및 근거

ORD 기록
ord-bbeec7b147a04622b97ec50f66b5c626
출처 데이터셋
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04889947

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