反应 #1483062

反应方程式

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

溶剂

acetone

反应条件

后处理

1. 1
   温度cooled with an ice bath
2. 2
   workup.ADDITIONwas added
3. 3
   workup.WAITAfter another 15 minutes
4. 4
   过滤was filtered through celite
5. 5
   其他the filtrate evaporated in vacuo
6. 6
   其他The residue was partitioned between 100 mL ether and 100 mL saturated ammonium chloride solution
7. 7
   萃取The aqueous layer was extracted with 100 mL ether
8. 8
   洗涤the combined ether solution washed with brine
9. 9
   干燥dried (MgSO4)
10. 10
    过滤filtered
11. 11
    其他evaporated

实验过程

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.

来源