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ChemicalBook CAS DataBase List ETHYL 3-ETHOXYBUT-2-ENOATE

ETHYL 3-ETHOXYBUT-2-ENOATE synthesis

14synthesis methods
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Yield: 85%

Reaction Conditions:

Stage #1:ethyl acetoacetate with sulfuric acid in ethanol at 50;Inert atmosphere;
Stage #2:orthoformic acid triethyl ester at 50; for 16 h;

Steps:

2
To a solution of ethylacetoacetate (2.7 kg, 20.74 mol) in ethanol (4 L) was added conc.H2S04 (4 ml) at 25 °C under a nitrogen atmosphere. The mixture was heated to 50 °C before adding triethylorthoformate (3073.6 g, 20.74 mol) drop wise. The mixture was stirred at 50 °C for 16h. The mixture was concentrated under reduced pressure to give the title compound (2.8 kg, 85 %) as a yellow oil. 1H NMR (400 MHz, CDCI3): δ 4.9 (s, 1 H), 4.1 (m, 2H), 3.7 (m, 2H), 2.2 (s, 3H), 1.2 (m, 3H), 1.1 (m, 3H).

References:

PFIZER LIMITED;BELL, Andrew Simon;GARDNER, Iain Brian;PRYDE, David Cameron;WAKENHUT, Florian Michel;GIBSON, Karl Richard WO2012/66442, 2012, A1 Location in patent:Page/Page column 23