반응 #4558

반응 방정식

acetic acid

DIBAL-H

4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester

ether

→

product

수율 74.0%

4-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-penten-1-ol

수율 74.0%

용매

toluene

water

toluene

반응 조건

후처리

1. 1
   기타the temperature below -60° C
2. 2
   기타the temperature below -60° C
3. 3
   온도to warm to room temperature
4. 4
   여과the solid material was filtered off
5. 5
   세척The filtrate was washed twice with saturated NaHCO3 and once with water
6. 6
   건조dried over MgSO4
7. 7
   기타the solvent was removed by rotary evaporation
8. 8
   기타The residue was purified by HPLC
9. 9
   세척eluting with 80:20 hexane

실험 절차

To a solution of 4.5 g (10.6 mmol) 4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester in 25 ml toluene at -78° C. was added dropwise over a period of 30 min, 16.5 ml of 1.5M DIBAL-H in toluene, keeping the temperature below -60° C. The mixture was stirred for 21/2 hours at -78° C. To the mixture was added 17 ml of a 75:25:6 ether:acetic acid:water mixture, keeping the temperature below -60° C. The mixture was then allowed to warm to room temperature and the solid material was filtered off. The filtrate was washed twice with saturated NaHCO3 and once with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC, eluting with 80:20 hexane:acetone, to give 3.1 g (74%) of the product as a pale yellow oil which was used immediately in the next reaction.

출처