反应 #4561

反应方程式

n-butyllithium

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

diisopropylamine

ethyl acetate

NH4Cl

→

product

收率 70.0%

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

收率 70.0%

溶剂

hexane

ether

ether

ether

反应条件

后处理

1. 1
   workup.ADDITIONwas slowly added
2. 2
   其他the aqueous phase separated
3. 3
   萃取extracted with ether
4. 4
   干燥The combined organic layers were dried over MgSO4
5. 5
   其他evaporated to dryness
6. 6
   其他the residue purified by prep LC
7. 7
   洗涤eluting with 85:15 hexane
8. 8
   其他The resulting colorless oil was thoroughly dried

实验过程

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.

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