Reaction #657306

Reaction equation

sodium hydride

4-fluoroacetophenone

diethylcarbonate

→

ethyl 3-(4-fluorophenyl)-3-oxopropanoate

Yield 83.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThereafter, the reaction is quenched with aqueous 10% HCl
2. 2
   Extractionextracted with ethyl acetate (2×100 mL)
3. 3
   DryingThe ethyl acetate layer is dried over anhydrous sodium sulphate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   OtherThe crude material is purified by column chromatography

Procedure

To a mixture of 4-fluoroacetophenone (20.0 g, 0.145 mol), ethanol (1 mL) and diethylcarbonate (100 mL) is added sodium hydride (60%, 12.0 g, 0.29 mol) at 0° C. portionwise over a period of 30 min. Afterwards the reaction mixture is allowed to warm to room temperature and stirred for 3 h. Thereafter, the reaction is quenched with aqueous 10% HCl and extracted with ethyl acetate (2×100 mL). The ethyl acetate layer is dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel (230-400 mesh) in ethyl acetate and hexane (1:99 to 5:95) as eluent and 25 g (83%) of ethyl 3-(4-fluorophenyl)-3-oxopropanoate are obtained as light yellow liquid.

Source