Sodium hydride → 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrile

HRID 2389903Notes

Reaction equation

HRID 2389903 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]3[CH2:25][CH2:24][C:23](=O)[C:21]3=2)[O:16][CH2:15]1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH2:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]3[CH2:25][CH2:24][C:23](=[CH:5][C:3]#[N:4])[C:21]3=2)[O:16][CH2:15]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 591793681,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

Product 1

HCID 666019131,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of 60% sodium hydride (137 mg, 3.42 mmol) in tetrahydrofuran (15 mL) was added diethyl cyanomethylphosphonate (600 μL, 3.71 mmol) under ice-cooling, and the mixture was stirred for 15 min. A solution of 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one (500 mg, 2.85 mmol) in tetrahydrofuran (15 mL) was added thereto, and the mixture was further stirred for 15 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate 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=30/70→80/20) to give the title compound (514 mg, yield 91%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 15 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=30/70→80/20)

Sources & evidence

ORD record
ord-bf81db4e8dfe44478c66e290c7ac3258
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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