Water → (E)-(6-methoxyindan-1-ylidene)acetonitrile

HRID 582200Notes

Reaction equation

HRID 582200 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][O:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][CH2:21][C:22]2=O)=[CH:18][CH:17]=1.O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[CH3:14][O:15][C:16]1[CH:24]=[C:23]2[C:19]([CH2:20][CH2:21]/[C:22]/2=[CH:5]\[C:3]#[N:4])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 11830118(E)-(6-methoxyindan-1-ylidene)acetonitrileYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a suspension of 60% sodium hydride (2.71 g, 67.9 mmol.) in tetrahydrofuran (150 ml) was added dropwise, under ice-cooling, diethyl cyanomethylphosphonate (11.5 g, 64.8 mmol.). The mixture was stirred for 15 minutes. To the reaction mixture was added dropwise a solution of 6-methoxy-1-indanone (10.0 g, 61.7 mmol.) in tetrahydrofuran (30 ml). The reaction mixture was stirred for 30 minutes at room temperature, which was poured into water, and then the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue thus obtained was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8), followed by recrystallization from ethyl acetate/hexane to afford the titled compound (6.00 g, yield 53%), m.p.95-96° C. (recrystallized from ethyl acetate/hexane).

Workup

  1. additionwas added dropwise, under ice-
  2. temperaturecooling
  3. stirringThe reaction mixture was stirred for 30 minutes at room temperature
  4. extractionthe organic substance was extracted with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8)
  10. customfollowed by recrystallization from ethyl acetate/hexane
  11. customto afford

Sources & evidence

ORD record
ord-04f13b0b5ca441a29f320cc9f92b9d1b
Source dataset
uspto-grants-1999_07
Patent number
US05922771

Reaction notes

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