Reaction #6072

Reaction equation

maleic anhydride

phenyl vinyl sulfide

ethylaluminum dichloride

→

title compound

Yield 90.7%

2,4-dioxo-6-phenylthio-3-oxabicyclo[3.2.0]heptane

Yield 90.7%

Solvents

1,2-dichloroethane

methylene chloride

Conditions

Workup

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

Procedure

To a solution of maleic anhydride (0.39 g, 4 mmol) and phenyl vinyl sulfide (0.52, 4 mmol) in 17 mL of 1,2-dichloroethane under nitrogen, was added 2 mL (0.5 equiv) of ethylaluminum dichloride. The resultant solution was stirred at ambient temperature for 0.5 h and then diluted with 75 mL of methylene chloride. The methylene chloride solution was washed three times with saturated aqueous ammonium chloride solution and once with brine, dried over anhydrous sodium sulfate and concentrated to give 0.85 g of the title compound; EI-MS, m/e (rel intensity): 234 (M+, 23), 136 (100), 109 (12), 91 (21).

Source