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

HRID 1882758Notes

Reaction equation

HRID 1882758 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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 (1 N), 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).

Workup

  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 (1 N), 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)

Sources & evidence

ORD record
ord-6ff660f59df1460bb4850d148162d887
Source dataset
uspto-grants-2004_07
Patent number
US06759409B2

Reaction notes

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