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

HRID 2389915Notes

Reaction equation

HRID 2389915 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH2:14]1[C:18]2=[C:19]3[C:25](=O)[CH2:24][CH2:23][C:20]3=[N:21][CH:22]=[C:17]2[O:16][CH2:15]1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH2:14]1[C:18]2=[C:19]3[C:20]([CH2:23][CH2:24]/[C:25]/3=[CH:3]\[C:1]#[N:2])=[N:21][CH:22]=[C:17]2[O:16][CH2:15]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 591794301,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-one

Product 1

HCID 59179421(2E)-1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylideneacetonitrileYield 60%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of diethyl cyanomethylphosphonate (757 mg, 4.27 mmol) in tetrahydrofuran (20 mL) was added 65% sodium hydride (137 mg, 3.71 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The mixture was added to a solution of 1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-one (500 mg, 2.85 mmol) in tetrahydrofuran (10 mL) under ice-cooling, and the mixture was stirred for 10 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by recrystallization (ethyl acetate) to give the title compound (337 mg, yield 60%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 10 min
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-5a935e28e3224d69b8d83bd2b5c5f30a
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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