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

HRID 1903616Notes

Reaction equation

HRID 1903616 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 mol) of mineral oil free sodium hydride in 1.2 liters of tetrahydrofuran were added dropwise 58.4 g (0.328 mol) of diethylcyanomethyl phosphonate. After the hydrogen evolution had ceased (ca 60 min.), 69.4 g (0.3 mol) of 2-benzyl-4-chlorobenzaldehyde, in 75 ml of tetrahydrofuran, were 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 over 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 over 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-aaca5dbfdd8e4ee9948631d588f851db
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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