Cesium carbonate → 2-Diazoindane-1,3-dione

HRID 490788

반응식

HRID 490788 반응식
[N-]=[N+:2]=[N-:3].[Na+].CS(Cl)(=O)=O.[C:10]1(=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12](=[O:19])[CH2:11]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[N+:2](=[C:11]1[C:10](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:19])=[N-:3]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 118151,3-IndandioneHCID 31297Methanesulfonyl chlorideHCID 33557Sodium Azide

생성물 1

HCID 41748362-Diazoindane-1,3-dione수율 42%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a suspension of sodium azide (2.4 g, 36.3 mmol) in CH3CN (73 mL) was added methanesulfonyl chloride (2.8 mL, 36.3 mmol). After stirring for 16 h, the reaction mixture was poured over a suspension of indan-1,3-dione (5.3 g, 36.3 mmol) and cesium carbonate (11.8 g, 36.3 mmol) in CH3CN (50 mL). The mixture was stirred until reaction was complete (2 h), and then filtered through Celite. The filter cake was washed with EtOAc and the organic solvents were removed in vacuo. The resulting gum was diluted with EtOAc and rinsed successively with NaOH (1N), H2O and brine. The organic layer was dried (MgSO4), evaporated and the crude oil purified by flash chromatography (SiO2, 50% hexane/EtOAc) to give 2-diazoindan-1,3-dione (2a) (2.6 g, 42% yield).

후처리

  1. stirringThe mixture was stirred until reaction
  2. custom(2 h)
  3. filtrationfiltered through Celite
  4. washThe filter cake was washed with EtOAc
  5. customthe organic solvents were removed in vacuo
  6. additionThe resulting gum was diluted with EtOAc
  7. washrinsed successively with NaOH (1N), H2O and brine
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated
  10. customthe crude oil purified by flash chromatography (SiO2, 50% hexane/EtOAc)

출처 및 근거

ORD 기록
ord-e16ca153abf448c994c361d28d5b71e1
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528167B2

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