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

HRID 5976

반응식

HRID 5976 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-48761c7d7d1e44d5995d8941f05c8bb3
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246931

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