Reacción #464498

Ecuación de reacción

hydrochloric acid

trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)ethylene

sodium hydride

trimethylsulfonium iodide

→

trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)cyclopropane

Rendimiento 18.0%

Disolventes

ethyl acetate

N,N-dimethylformamide

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for 2 hours
2. 2
   LavadoThe organic layer was washed with water, saturated sodium bicarbonate aqueous solution, and brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   OtroThe solution was evaporated
5. 5
   Otrothe residue was chromatographed (hexane:ethyl acetate=4:1)

Procedimiento

To a solution of sodium hydride (1.0 g, 60% in oil) in N,N-dimethylformamide (50 ml) was added trimethylsulfonium iodide (6.1 g) at ambient temperature under N2 and stirred for 20 minutes. To the solution was added dropwise a solution of trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)ethylene (5.2 g) in N,N-dimethylformamide (10 ml) and stirred for 2 hours. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and 1N-hydrochloric acid (100 ml). The organic layer was washed with water, saturated sodium bicarbonate aqueous solution, and brine, and then dried over magnesium sulfate. The solution was evaporated and the residue was chromatographed (hexane:ethyl acetate=4:1) to give trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)cyclopropane (1.0 g).

Fuente