Sodium hydride → (2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrile

HRID 340674Notes

Reaction equation

HRID 340674 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][C:15]1[O:16][C:17]2[C:26]3[C:25](=O)[CH2:24][CH2:23][C:22]=3[CH:21]=[CH:20][C:18]=2[N:19]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:14][C:15]1[O:16][C:17]2[C:26]3[C:25](=[CH:5][C:3]#[N:4])[CH2:24][CH2:23][C:22]=3[CH:21]=[CH:20][C:18]=2[N:19]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 577812772-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

Product 1

HCID 67353411(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)acetonitrileYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 60% sodium hydride (90.0 mg, 2.24 mmol) in tetrahydrofuran (9 mL) was added diethyl cyanomethylphosphonate (393 μL, 2.43 mmol) under ice-cooling, and the mixture was stirred for 15 min. Thereto was added a solution of 2-methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (350 mg, 1.87 mmol) in tetrahydrofuran (9 mL), and the mixture was further stirred for 1 hr. 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 (300 mg, yield 76%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 1 hr
  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-efade831e38c4334b92a2e1e583f033e
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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