Tetrahydrofuran → HCID 16092064, compound

HRID 897383Notes

Reaction equation

HRID 897383 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 30 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. waitcontinued for 1 h
  2. customThe reaction was quenched by the addition of water
  3. extractionextracted with dichloromethane
  4. customby drying
  5. customevaporation of the organic solution

Sources & evidence

ORD record
ord-f3c1f2ae8b1147a192d80f252a11297e
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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