Reaktion #70654

Reaktionsgleichung

2-[2-(4-bromophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]-1H-isoindole-1,3(2H)-dione

Toluenesulfonic acid monohydrate

→

2-[1-(4-bromophenyl)-3-oxocyclobutyl]-1H-isoindole-1,3(2H)-dione

Lösungsmittel

EtOAc

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 2 days
2. 2
   Waschenwashed with sat. NaHCO3
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel chromatography
7. 7
   Wascheneluting with 0˜100% EtOAc in hexane

Vorschrift

A mixture of 2-[2-(4-bromophenyl)-5,8-dioxaspiro[3.4]oct-2-yl]-1H-isoindole-1,3(2H)-dione (8-2) (3.1 g, 7.48 mmol) and Toluenesulfonic acid monohydrate (0.14 g, 0.75 mmol) in acetone (50 mL) was refluxed for 2 days. The cooled mixture was diluted with EtOAc, washed with sat. NaHCO3, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with 0˜100% EtOAc in hexane, to give 2-[1-(4-bromophenyl)-3-oxocyclobutyl]-1H-isoindole-1,3(2H)-dione (8-3) as a colorless form.

Quelle