تفاعل #4558

معادلة التفاعل

acetic acid

DIBAL-H

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

ether

→

product

المردود 74.0%

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

المردود 74.0%

المذيبات

toluene

water

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىthe temperature below -60° C
2. 2
   أخرىthe temperature below -60° C
3. 3
   درجة الحرارةto warm to room temperature
4. 4
   ترشيحthe solid material was filtered off
5. 5
   غسيلThe filtrate was washed twice with saturated NaHCO3 and once with water
6. 6
   تجفيفdried over MgSO4
7. 7
   أخرىthe solvent was removed by rotary evaporation
8. 8
   أخرىThe residue was purified by HPLC
9. 9
   غسيلeluting with 80:20 hexane

الإجراء التجريبي

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.

المصدر