Reacción #6071

Ecuación de reacción

dimethyl maleate

phenyl vinyl sulfide

ethylaluminum dichloride

hexane

→

title compound

Dimethyl 3-phenylthiocyclobutane-1,2-dicarboxylate

Disolventes

1,2-dichloroethane

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe methylene chloride solution was washed three times with saturated aqueous ammonium chloride
2. 2
   Secadoonce with brine, dried over anhydrous sodium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated

Procedimiento

To a solution of dimethyl maleate (0.50 mL, 4 mmol) and phenyl vinyl sulfide (0.52 mL, 4 mmol) in 17 mL of 1,2-dichloroethane under nitrogen atmosphere, was added 1 equivalent (4 mL of a 1 M solution in hexane) of ethylaluminum dichloride. The resultant solution was heated at 85° C. for 18 h and then diluted with 75 mL of methylene chloride. The methylene chloride solution was washed three times with saturated aqueous ammonium chloride and once with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 0.98 g of the title compound; EI-MS, m/e (rel intensity): 280 (M+, 14), 136 (100).

Fuente