Reacción #710528

Ecuación de reacción

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

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours
2. 2
   Temperaturarefluxed for 5 hours
3. 3
   TemperaturaIt was then cooled to 0° C.
4. 4
   Otroquenched by NH4Cl solution
5. 5
   workup.STIRRINGwith stirring for 30 minutes
6. 6
   ExtracciónThe reaction mixture was then extracted with diethyl ether
7. 7
   LavadoThe ether layer was washed with distilled water
8. 8
   Secadodried over anhydrous sodium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated
11. 11
    OtroPurification on silica gel column

Procedimiento

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.

Fuente