반응 #487504

반응 방정식

isopropyl alcohol

isopropyl alcohol

( 28 )

Acetic acid 7-(tert-butyl-dimethyl-silanyloxy)-hept-2-ynyl ester

Jones Reagent

→

oil

7-Acetoxy-hept-5-ynoic acid

용매

acetone

반응 조건

후처리

1. 1
   온도cooled with an ice bath
2. 2
   workup.ADDITIONwas added
3. 3
   workup.WAITAfter another 15 minutes
4. 4
   여과was filtered through celite
5. 5
   기타the filtrate evaporated in vacuo
6. 6
   기타The residue was partitioned between 100 mL ether and 100 mL saturated ammonium chloride solution
7. 7
   추출The aqueous layer was extracted with 100 mL ether
8. 8
   세척the combined ether solution washed with brine
9. 9
   건조dried (MgSO4)
10. 10
    여과filtered
11. 11
    기타evaporated

실험 절차

A solution of crude (28) in acetone (100 mL) was treated with Jones Reagent (18.0 mL, 41.4 mmol, 2.3 M) and cooled with an ice bath. After 1 hour at room temperature, 10 mL isopropyl alcohol was added and the mixture stirred for 15 minutes. The mixture still had a brown color so another 10 mL isopropyl alcohol was added. After another 15 minutes, the color had not changed so the mixture was filtered through celite and the filtrate evaporated in vacuo. The residue was partitioned between 100 mL ether and 100 mL saturated ammonium chloride solution. The aqueous layer was extracted with 100 mL ether and the combined ether solution washed with brine and then dried (MgSO4), filtered and evaporated to leave a yellow oil (6.333 g) that was used directly in the next step.

출처