反応 #59441

反応方程式

(1-naphthalenylmethylene)-propanedinitrile

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

ortho-tolyl magnesium bromide

→

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

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONTo this stirred solution was added, at room temperature
2. 2
   その他after which it was quenched with 1 N hydrochloric acid
3. 3
   洗浄The organic layer was washed with saturated aqueous sodium bicarbonate, brine
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated to dryness
7. 7
   その他purification on silica (20% ethyl acetate/hexanes) 455 mg product
8. 8
   その他was isolated as an off white foam

実験手順

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.

出典