Reaction #45867

Reaction equation

7-(1-allylbut-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

→

compound

Yield 76.0%

7-(Cyclopent-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Yield 76.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   Otherthe solvent was evaporated away under reduced pressure
3. 3
   OtherThe residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Procedure

At room temperature, Grubbs catalyst second generation (92 mg, 0.11 mol) was added to a solution of 7-(1-allylbut-3-enyl)-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-299) (400 mg, 1.09 mmol) dissolved in dichloromethane; (108 ml). Under nitrogen atmosphere, the solution was stirred at 50° C. for 3.5 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=9:1, v/v) to obtain the entitled compound (282 mg, 76%) as a white solid.

Source