反応 #4561

反応方程式

n-butyllithium

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

diisopropylamine

ethyl acetate

NH4Cl

→

product

収率 70.0%

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

収率 70.0%

溶媒

hexane

ether

ether

ether

反応条件

後処理

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

実験手順

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.

出典