Sodium hydride → 3-[4-(Methylthio)phenyl]acrylonitrile

HRID 654773

Reaction equation

HRID 654773 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][S:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>O1CCCC1.C(OCC)(=O)C>[CH3:14][S:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH:3][C:1]#[N:2])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 42396803-[4-(Methylthio)phenyl]acrylonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A solution of diethyl cyanomethylphosphonate (5.3 ml) in tetrahydrofuran (10 ml) was added dropwise to an ice-cooled mixture of sodium hydride (60%, 1.3 g) in tetrahydrofuran (40 ml). The mixture was stirred at 5° C. for 15 minutes. To the resulting mixture was added a solution of 4-(methylthio)benzaldehyde (5 g) in tetrahydrofuran (10 ml) at 5 to 10° C. The mixture was stirred at ambient temperature for 5 hours, diluted with ethyl acetate, and washed with water. The organic layer was dried and concentrated under reduced pressure. The residue was washed with a small amount of ether and dried to give pale brown crystals of 3-[4-(methylthio)phenyl]acrylonitrile (4.7 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at ambient temperature for 5 hours
  3. washwashed with water
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with a small amount of ether
  7. customdried

Sources & evidence

ORD record
ord-c0880880e1664f4ab2ec04aeec09e746
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Linked notes

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