Toluene → 1,2,6,7-tetrahydro-8H-indeno-(5,4-B)-furan-8-ylidene acetonitrile

HRID 420901Notes

Reaction equation

HRID 420901 reaction equation
C1(C)C=CC=CC=1.[CH2:8]1[CH2:12][O:11][C:10]2[CH:13]=[CH:14][C:15]3[CH2:16][CH2:17][C:18](=O)[C:19]=3[C:9]1=2.[C:21]([CH2:23]P(=O)(OCC)OCC)#[N:22].C[O-].[Na+]>CO.O>[CH2:8]1[CH2:12][O:11][C:10]2[CH:13]=[CH:14][C:15]3[CH2:16][CH2:17]/[C:18](=[CH:23]\[C:21]#[N:22])/[C:19]=3[C:9]1=2

Participants

7

Reactant 4

HCID 1140TolueneHCID 75676Diethyl (cyanomethyl)phosphonateHCID 10942334Sodium MethoxideHCID 111376161,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

Product 1

HCID 118303811,2,6,7-tetrahydro-8H-indeno-(5,4-B)-furan-8-ylidene acetonitrileYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution of toluene (184 g), 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (8.5 g, 48.9 mmol) and diethyl cyanomethylphosphonate (10.4 g, 58.7 mmol) was added dropwise 28% sodium methoxide solution in methanol (11.3 g) over 1 hr under ice-cooling, and reacted for 4 hrs. To the reaction solution was added dropwise water (85 μg), and warmed, then the layers were separated. The organic layer was washed with water, and filtered to remove dusts under pressurization. The organic layer was concentrated under reduced pressure, and to the residue was added methanol and concentrated under reduced pressure to substitute the solvent. After stirring for 1 hr under heating with reflux, the solution was cooled and matured for 1 hr. The crystallization solution was filtered, and the crystals were dried under reduced pressure to give title compound (amount 8.1 g, yield 84.4%).

Workup

  1. temperaturecooling
  2. customreacted for 4 hrs
  3. temperaturewarmed
  4. customthe layers were separated
  5. washThe organic layer was washed with water
  6. filtrationfiltered
  7. customto remove dusts under pressurization
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. additionto the residue was added methanol
  10. concentrationconcentrated under reduced pressure
  11. temperatureunder heating
  12. temperaturewith reflux
  13. temperaturethe solution was cooled
  14. waitmatured for 1 hr
  15. filtrationThe crystallization solution was filtered
  16. customthe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-71450a7f3fd7416abdf312eb7d30bee7
Source dataset
uspto-grants-2012_01
Patent number
US08097737B2

Reaction notes

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