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ETHYL 2-(2-OXO-2H-CHROMEN-7-YLOXY)ACETATE synthesis

2synthesis methods
-

Yield:72000-18-1 96%

Reaction Conditions:

Stage #1: 7-hydroxy-2H-chromen-2-onewith potassium carbonate in acetone; for 0.5 h;
Stage #2: ethyl bromoacetate in ethyl acetate at 20; for 6 h;

Steps:

4.1.Preparation of 6, 12 and 18 (Scheme 1f)

General procedure: 0.4g of SM1 (2.2mmol), SM2 (2.4mmol) and SM3 (2.2mmol), respectively, were dissolved in acetone (2.0mL) and 1.75 or 3.5 molar equivalents of K2CO3 was add, and stirred during thirty min. After that, it was added drop wise 1.75 molar equivalents of ethyl bromoacetate. The mixture was reacted at room temperature during 6h for compounds 6 and 12, and 8h for 18. After reactions were completed (analyzed by TLC), the solid was filtered off and dried to afford the corresponding compounds 6 ethyl {[6-(2-ethoxy-2-oxoethoxy)-2-oxo-2H-chromen-7-yl]oxy}acetate, 12 [ethyl 2-(2-oxo-2H-chromen-7-yloxy)acetate] and 18 [ethyl 2-(4-methyl-2-oxo-2H-chromen-7-yloxy)acetate].

References:

Sánchez-Recillas, Amanda;Navarrete-Vázquez, Gabriel;Hidalgo-Figueroa, Sergio;Rios, María Yolanda;Ibarra-Barajas, Maximiliano;Estrada-Soto, Samuel [European Journal of Medicinal Chemistry,2014,vol. 77,p. 400 - 408]