반응 #933370

반응 방정식

diethylaluminum chloride

t-butyl bromoacetate

2-dodecylbenzaldehyde

→

desired product

수율 79.0%

t-Butyl 3-hydroxy-3-(2-dodecylphenyl)propionate

수율 79.0%

용매

tetrahydrofuran

tetrahydrofuran

hexane

반응 조건

후처리

1. 1
   온도to warm slowly to room temperature
2. 2
   여과The mixture was filtered
3. 3
   기타to remove zinc
4. 4
   농축concentrated
5. 5
   추출extracted with ether
6. 6
   건조Organic extracts were dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타to afford crude product
10. 10
    기타flash chromatographed on silica using 8% ethyl acetate in hexane

실험 절차

A solution of diethylaluminum chloride (54.7 mmol) in hexane was added to a slurry of zinc dust (74.5 mmol) and a catalytic amount of copper (I) bromide (2.5 mmol) in anhydrous tetrahydrofuran (300 ml) while stirring under argon at 20° C. The resulting mixture was then cooled to 0° C. in an ice-methanol bath. A solution of t-butyl bromoacetate (49.8 mmol) and 2-dodecylbenzaldehyde of Example 1(c) (54.7 mmol); in anhydrous tetrahydrofuran was added slowly over 60 minutes. The reaction was stirred for about 24 hours and was permitted to warm slowly to room temperature. The mixture was filtered to remove zinc, concentrated, acidified with 3N hydrochloric acid and extracted with ether. Organic extracts were dried over magnesium sulfate, filtered, and evaporated to afford crude product. This material was then flash chromatographed on silica using 8% ethyl acetate in hexane to give the desired product in 79% yield.

출처