Hydrochloric Acid → 3-phenylpropyl 4-(2-(N,N-diethylamino)ethoxy)acetoacetate

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Reaction Steps

N,N-Diethylaminoethanol (7.49 mL, 56.6 mmol) in THF (25 mL) was added dropwise to a suspension of sodium hydride (3.5 g, 87.5 mmol) in THF (100 mL) at 0° C. The mixture was then stirred for 30 minutes at room temperature, cooled to 0° C., 3-phenylpropyl 4-chloroacetoacetate (11.10 mL, 51.5 mmol) in THF (25 mL) was added dropwise and the reaction mixture was then stirred for 18 h whilst warming to room temperature. 1N Hydrochloric acid was added until the mixture was acidic and the aqueous layer was then separated. The organic layer was extracted twice more with 1N hydrochloric acid. The combined acid layers were washed two times with ethyl acetate and then made basic to pH 8 with sodium hydrogen carbonate and extracted with chloroform three times. The combined extracts were washed with brine, dried and evaporated to give the title compound (16.3 g) as an oil. Electrospray MS m/z 336 [M+H]+.

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