Reaktion #361268

Reaktionsgleichung

piperonal

trimethylsulfonium iodide

potassium tert-butoxide

water

→

3,4-methylenedioxyphenyloxirane

Ausbeute 91.5%

Lösungsmittel

tetrahydrofuran

dimethyl sulfoxide

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturwas maintained below 5° C
3. 3
   Extraktionextracted once with ethyl acetate
4. 4
   WaschenThe extract was washed twice with water and once with brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo

Vorschrift

To an ice-cooled suspension of potassium tert-butoxide (0.82 g) in tetrahydrofuran (6.6 ml) was added trimethylsulfonium iodide (98% purity; 1.5 g) in dimethyl sulfoxide (6.6 ml). After the addition was complete, piperonal (1.0 g) in tetrahydrofuran (3.3 ml) was added dropwise to the mixture while the internal temperature was maintained below 5° C. After stirring at ambient temperature for 1 hour, the mixture was poured into water and extracted once with ethyl acetate. The extract was washed twice with water and once with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 3,4-methylenedioxyphenyloxirane (1.0 g), which was used for next reaction without further purification.

Quelle