Реакция #710528

Уравнение реакции

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

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours
2. 2
   Температураrefluxed for 5 hours
3. 3
   ТемператураIt was then cooled to 0° C.
4. 4
   Другоеquenched by NH4Cl solution
5. 5
   workup.STIRRINGwith stirring for 30 minutes
6. 6
   ЭкстракцияThe reaction mixture was then extracted with diethyl ether
7. 7
   ПромывкаThe ether layer was washed with distilled water
8. 8
   Сушкаdried over anhydrous sodium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    Другоеevaporated
11. 11
    ДругоеPurification on silica gel column

Методика

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.

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