Reaction #487504

Reaction equation

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

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturecooled with an ice bath
2. 2
   workup.ADDITIONwas added
3. 3
   workup.WAITAfter another 15 minutes
4. 4
   Filtrationwas filtered through celite
5. 5
   Otherthe filtrate evaporated in vacuo
6. 6
   OtherThe residue was partitioned between 100 mL ether and 100 mL saturated ammonium chloride solution
7. 7
   ExtractionThe aqueous layer was extracted with 100 mL ether
8. 8
   Washthe combined ether solution washed with brine
9. 9
   Dryingdried (MgSO4)
10. 10
    Filtrationfiltered
11. 11
    Otherevaporated

Procedure

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.

Source