Water → (6-Methoxyindan-1-ylidene) acetonitrile

HRID 1977987Notes

Reaction equation

HRID 1977987 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>C1COCC1>[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

6

Reactant 4

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

Product 1

HCID 53954914(6-Methoxyindan-1-ylidene) acetonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 60% sodium hydride (2.71 g, 67.9 mmol) in THF (150 ml) was added dropwise, under ice-cooling, diethyl cyanomethylphosphonate (11.5 g, 64.8 mmol). The mixture was stirred for 15 hours, to which was then added dropwise a solution of 6-methoxy-1-indanone (10.0 g, 61.7 mmol) in THF (30 ml). The reaction mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into water, and the organic layer was subjected to extraction with ethyl acetate. The extract solution was washed with brine and water, followed by drying over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=8:2). Recrystallization of the product-from ethyl acetate/hexane afforded the above-titled compound (6.00 g, yield 53%).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 30 minutes at room temperature
  3. extractionthe organic layer was subjected to extraction with ethyl acetate
  4. washThe extract solution was washed with brine and water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=8:2)
  8. customRecrystallization of the product-from ethyl acetate/hexane

Sources & evidence

ORD record
ord-92130f1b6f304db881c45fd69cf1ccb9
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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