반응 #4561

반응 방정식

n-butyllithium

2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanaldehyde

diisopropylamine

ethyl acetate

NH4Cl

→

product

수율 70.0%

4-(4-(4-Bromo-2-fluorophenoxy)phenoxy)-3-hydroxypentanoate ethyl ester

수율 70.0%

용매

hexane

ether

ether

ether

반응 조건

후처리

1. 1
   workup.ADDITIONwas slowly added
2. 2
   기타the aqueous phase separated
3. 3
   추출extracted with ether
4. 4
   건조The combined organic layers were dried over MgSO4
5. 5
   기타evaporated to dryness
6. 6
   기타the residue purified by prep LC
7. 7
   세척eluting with 85:15 hexane
8. 8
   기타The resulting colorless oil was thoroughly dried

실험 절차

A solution of 1.54 ml (11 mmol) of diisopropylamine in 20 ml of ether was cooled under N2 to -78° C. and 6.9 ml (11 mmol) of 1.6M n-butyllithium in hexane was slowly added. After 15 min of -78° C. 0.97 g (11 mmol) of ethyl acetate in 3 ml of ether was added dropwise. The resulting mixture was stirred at -78° C. for 15 min when a solution of 3.39 g (10 mmol) of 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanaldehyde in 5 ml of ether was slowly added. The mixture was allowed to warm to room temperature, poured into aqueous NH4Cl and the aqueous phase separated and extracted with ether. The combined organic layers were dried over MgSO4 and evaporated to dryness and the residue purified by prep LC, eluting with 85:15 hexane:acetone. The resulting colorless oil was thoroughly dried to leave 2.99 g of product. Structure was confirmed by IR and NMR analysis. Calc. for C17H20BrFO5 : C, 53.41, H, 4.72. Found: C, 53.10, H, 4.66.

출처