Réaction #6071

Équation de réaction

dimethyl maleate

phenyl vinyl sulfide

ethylaluminum dichloride

hexane

→

title compound

Dimethyl 3-phenylthiocyclobutane-1,2-dicarboxylate

Solvants

1,2-dichloroethane

methylene chloride

Conditions de réaction

Traitement

1. 1
   LavageThe methylene chloride solution was washed three times with saturated aqueous ammonium chloride
2. 2
   Séchageonce with brine, dried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Mode opératoire

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).

Source