Reaktion #710528

Reaktionsgleichung

Compound I

2-(1,3-benzodioxol-5-yl)-2-methyl propanal

t-BuOK

→

desired Compound

5-(2-methylbut-3-en-2-yl)benzo[d][1,3]dioxole

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours
2. 2
   Temperaturrefluxed for 5 hours
3. 3
   TemperaturIt was then cooled to 0° C.
4. 4
   Sonstigequenched by NH4Cl solution
5. 5
   workup.STIRRINGwith stirring for 30 minutes
6. 6
   ExtraktionThe reaction mixture was then extracted with diethyl ether
7. 7
   WaschenThe ether layer was washed with distilled water
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    SonstigePurification on silica gel column

Vorschrift

A suspension of methyl triphenyl phosphonium bromide (325 mg, 0.95 mmol) and t-BuOK (87.5 mg, 0.78 mmol) in dry tetrahydrofuran (1 mL) was stirred at 0° C. for 1 hour. To this mixture at 0° C., a solution of Compound I (50 mg, 0.26 mmol) in dry tetrahydrofuran (1 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours and then refluxed for 5 hours. It was then cooled to 0° C. and quenched by NH4Cl solution with stirring for 30 minutes. The reaction mixture was then extracted with diethyl ether. The ether layer was washed with distilled water, dried over anhydrous sodium sulfate, filtered and evaporated. Purification on silica gel column using petroleum ether followed by with 20:1 petroleum ether-ethyl acetate afforded desired Compound No. 14 (1 mg) as colourless oil.

Quelle