Sodium hydride → (4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrile

HRID 1661384Notes

Reaction equation

HRID 1661384 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[Br:14][C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([O:27][CH3:28])=[C:20]2[C:16]=1[CH2:17][CH2:18][C:19]2=O.[Cl-].[NH4+]>O1CCCC1>[Br:14][C:15]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[C:21]([O:27][CH3:28])=[C:20]2[C:16]=1[CH2:17][CH2:18][C:19]2=[CH:5][C:3]#[N:4]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 577812634-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 67355123(4-Bromo-7-methoxy-6-nitro-2,3-dihydro-1H-inden-1-ylidene)acetonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride (1.03 g, 25.6 mmol) in tetrahydrofuran (100 mL) was added diethyl cyanomethylphosphonate (4.52 mL, 28.0 mmol) under ice-cooling, and the mixture was stirred for 15 min. Thereto was added a solution of 4-bromo-7-methoxy-6-nitroindan-1-one (6.67 g, 23.3 mmol) in tetrahydrofuran (50 mL), and the mixture was further stirred for 30 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (5.54 g, yield 77%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

Sources & evidence

ORD record
ord-e05f8ad23940425399f8866afade0e4f
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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