Sodium hydride → 3-(2-Benzyl-4-chlorophenyl)prop-2-enenitrile

HRID 647610Notes

Reaction equation

HRID 647610 reaction equation
[H-].[Na+].P(=O)([O-])O[C:5](CC)(CC)[C:6]#[N:7].[H][H].[CH2:16]([C:23]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:24]=1[CH:25]=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[CH2:16]([C:23]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:24]=1[CH:25]=[CH:5][C:6]#[N:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 155700672-Benzyl-4-chlorobenzaldehydeHCID 178418361HCID 178418361, compoundHCID 178449162HCID 178449162, compound

Product 1

HCID 545603803-(2-Benzyl-4-chlorophenyl)prop-2-enenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 10.5 g (0.437 mole) of mineral oil free sodium hydride in 1.2 liters of tetrahydrofuran was added dropwise 58.4 g (0.328 mole) of diethylcyanomethyl phosphonate. After the hydrogen evolution had ceased ca 60 min, 69.4 g (0.3 mole) of 2-benzyl-4-chlorobenzaldehyde, in 75 ml of tetrahydrofuran was added dropwise. The mixture was stirred overnight at room temperature. The tetrahydrofuran solution was decanted, and concentrated at room temperature. The residue was partitioned between 2 liters of water and 1.5 liters of ether. The ether solution was separated, washed with water, and dried with sodium sulfate. The ether was removed at reduced pressure to give a yellow oil which was used without further purification.

Workup

  1. customThe tetrahydrofuran solution was decanted
  2. concentrationconcentrated at room temperature
  3. customThe residue was partitioned between 2 liters of water and 1.5 liters of ether
  4. customThe ether solution was separated
  5. washwashed with water
  6. dry with materialdried with sodium sulfate
  7. customThe ether was removed at reduced pressure
  8. customto give a yellow oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-a9d04aa08cc14aeaa8529df355ae2e52
Source dataset
uspto-grants-1983_10
Patent number
US04409390

Reaction notes

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