Maleic Anhydride → 2,4-Dioxo-6-phenylthio-3-oxabicyclo[3.2.0]heptane

HRID 5976

Reaction equation

HRID 5976 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH:8]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:9].[Cl-].[Cl-].C([Al+2])C>ClCCCl.C(Cl)Cl>[O:5]=[C:4]1[O:6][C:1](=[O:7])[CH:2]2[CH:3]1[CH2:9][CH:8]2[S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 7923Maleic AnhydrideHCID 74572Phenyl Vinyl SulfideHCID 16686341Ethyl aluminium dichloride

Product 1

HCID 197942712,4-Dioxo-6-phenylthio-3-oxabicyclo[3.2.0]heptaneYield 90.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

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).

Workup

  1. washThe methylene chloride solution was washed three times with saturated aqueous ammonium chloride solution
  2. dry with materialonce with brine, dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-48761c7d7d1e44d5995d8941f05c8bb3
Source dataset
uspto-grants-1993_09
Patent number
US05246931

Linked notes

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