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

HRID 5976

反応式

HRID 5976 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-48761c7d7d1e44d5995d8941f05c8bb3
出典データセット
uspto-grants-1993_09
特許番号
US05246931

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