Reaction #6071

Reaction equation

dimethyl maleate

phenyl vinyl sulfide

ethylaluminum dichloride

hexane

→

title compound

Dimethyl 3-phenylthiocyclobutane-1,2-dicarboxylate

Solvents

1,2-dichloroethane

methylene chloride

Conditions

Workup

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

Procedure

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