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ChemicalBook CAS DataBase List 2-(4-FLUOROBENZYL)ACETOACETIC ACID ETHYL ESTER
88023-07-8

2-(4-FLUOROBENZYL)ACETOACETIC ACID ETHYL ESTER synthesis

2synthesis methods
-

Yield:88023-07-8 97%

Reaction Conditions:

Stage #1: ethyl 3-oxobutanoatewith sodium hydride in tetrahydrofuran at 0 - 60; for 0.5 h;
Stage #2: 4-Fluorobenzyl bromide in tetrahydrofuran at 20 - 25;

Steps:

General Procedure for the Preparation of 2-5b.

General procedure: In an ice bath, a reaction solution of60% NaH (680 mg, 17 mmol) in dry THF (40 mL) was stirred for 10 min. Ethyl acetoacetate(2.2 mL, 17 mmol) was added dropwise. After stirring the reaction for 30 min, startingmaterials 2-5a (15.3 mmol) were added and continued reaction at room temperature in theTLC monitor. After the reaction finished, the solids were filtered out, most of the solventswere removed, and water (100 mL) was added. The mixture was extracted with ethyl acetate,washed with saturated salt, dried over anhydrous sodium sulfate, and evaporatedin vacuo to get compounds 2-5b. These products were directly used as the next reactantswithout any further purification.

References:

Yu, Zhihui;Li, Mengru;Guo, Shiqi;Wang, Weijie;Qu, Feng;Ma, Yulei;Liu, Hongrui;Chen, Ying [Molecules,2022,vol. 27,# 13,art. no. 4021]