반응 #710528

반응 방정식

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

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours
2. 2
   온도refluxed for 5 hours
3. 3
   온도It was then cooled to 0° C.
4. 4
   기타quenched by NH4Cl solution
5. 5
   workup.STIRRINGwith stirring for 30 minutes
6. 6
   추출The reaction mixture was then extracted with diethyl ether
7. 7
   세척The ether layer was washed with distilled water
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   여과filtered
10. 10
    기타evaporated
11. 11
    기타Purification on silica gel column

실험 절차

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.

출처