Tetrahydrofuran → HCID 16092064, compound

HRID 2229772Notes

Reaction equation

HRID 2229772 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1C=O.O1CCC[CH2:24]1>>[CH3:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:3](=[CH2:24])[C:1]#[N:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 107222-MethylbenzaldehydeHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 16092064HCID 16092064, compound

Procedure

Diethyl cyanomethylphosphonate (5.0 ml, 30.9 mmol) was added to a stirring suspension of sodium hydride (60% oily suspension, 1.24 g, 31 mmol) in tetrahydrofuran (50 ml) under argon. After 3o min, 2-methylbenzaldehyde (3.6 ml, 31.1 mmol) was added and stirring continued for 1 h. The reaction was quenched by the addition of water and extracted with dichloromethane followed by drying and evaporation of the organic solution. Column chromatography (hexane; hexane:ethylacetate=3:1) provided 2-(2-methylphenyl)acrylonitrile as an oil. This material (3.8 g), 10% palladium on carbon (3.8 g) and 12 N hydrochloric acid (11.8 ml, 142 mmol) in methanol (125 ml) were hydrogenated with hydrogen at atmospheric pressure for 2 d. The catalyst was removed by filtration and the solvent was evaporated. The resultant material was partitioned between dichloromethane and water. The aqueous layer was made basic with 10 N sodium hydroxide and extracted with dichloromethane, followed by drying and evaporation. The resultant material was purified on a silica gel column (chloroform:methanol:triethylamine=85:10:5) to provide the title compound as an oil.

Workup

  1. customThe reaction was quenched by the addition of water
  2. extractionextracted with dichloromethane
  3. customby drying
  4. customevaporation of the organic solution

Sources & evidence

ORD record
ord-fb9009db9d6b49f28de4d1e7ee5e623e
Source dataset
uspto-grants-2002_07
Patent number
US06420385B1

Reaction notes

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