Sodium hydride → (6,7-Dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile

HRID 1802674Notes

Reaction equation

HRID 1802674 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[O:14]1[C:18]2[C:19]3[C:20](=O)[CH2:21][CH2:22][C:23]=3[CH:24]=[CH:25][C:17]=2[N:16]=[CH:15]1.[Cl-].[NH4+]>O1CCCC1>[O:14]1[C:18]2[C:19]3[C:20](=[CH:5][C:3]#[N:4])[CH2:21][CH2:22][C:23]=3[CH:24]=[CH:25][C:17]=2[N:16]=[CH:15]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 577812656H-Indeno[5,4-d]oxazol-8(7H)-one

Product 1

HCID 67353458(6,7-Dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrileYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride (73.4 mg, 1.84 mmol) in tetrahydrofuran (8 mL) was added diethyl cyanomethylphosphonate (322 μL, 1.99 mmol) under ice-cooling, and the mixture was stirred for 15 min. Thereto was added a solution of 6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (265 mg, 1.53 mmol) in tetrahydrofuran (8 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 (220 mg, yield 73%).

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-fdc5b811563d469bba320649de513e5d
Source dataset
uspto-grants-2013_01
Patent number
US08349879B2

Reaction notes

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