Réaction #59441

Équation de réaction

(1-naphthalenylmethylene)-propanedinitrile

2-[(3-Methoxyphenyl)(1-naphthyl)methyl]malononitrile

ortho-tolyl magnesium bromide

→

2-[(2-Methylphenyl)(1-naphthyl)methyl]malononitrile

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONTo this stirred solution was added, at room temperature
2. 2
   Autreafter which it was quenched with 1 N hydrochloric acid
3. 3
   LavageThe organic layer was washed with saturated aqueous sodium bicarbonate, brine
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated to dryness
7. 7
   Autrepurification on silica (20% ethyl acetate/hexanes) 455 mg product
8. 8
   Autrewas isolated as an off white foam

Mode opératoire

A flask was charged with (1-naphthalenylmethylene)-propanedinitrile of Example 3 (408 mg, 2 mmol) and 10 mL anhydrous tetrahydrofuran. To this stirred solution was added, at room temperature, ortho-tolyl magnesium bromide (1.2 mL, 2.4 mmol, 2 M in tetrahydrofuran). The reaction was stirred 1.5 hours, after which it was quenched with 1 N hydrochloric acid and taken up in ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and evaporated to dryness. Following purification on silica (20% ethyl acetate/hexanes) 455 mg product was isolated as an off white foam.

Source