Yield:63131-29-3 93%

Reaction Conditions:

with sodium hydride in toluene;mineral oil at 20 - 110; for 13 h;Inert atmosphere;

Steps:

2 5.3. General procedure for the synthesis of aryl β-keto esters 9a-c
General procedure: A solution of the appropriate acetophenone derivative 8a-c (10g) in dry 117 PhCH₃ (50mL) was added dropwise to a suspension of 136 NaH (4 equiv., 60% 137 mineral oil dispersion) and 12 dimethyl carbonate (3 equiv.) in dry PhCH₃ (80mL) over 1h with stirring at room temperature under argon protective atmosphere. Thus composed reaction mixture was vigorously stirred by means of mechanical stirrer at 110°C for 12h. Next, the content of the flask was spilled into a beaker (V=1L), cooled to 0-5°C, and the thick suspension formed was carefully diluted with a solution of 36% 33 HCl (30mL) in ice-cold 15 H₂O (150mL). The aqueous solution was extracted with AcOEt (3×100mL), the organic layers combined were neutralized by washing them with saturated aqueous NaHCO₃ solution (2×100mL), and subsequently dried over Na₂SO₄. The volatiles were then removed under reduced pressure, and the crude material was purified by vacuum distillation to give the respective products 14 9a-c as oils.

References:

Borowiecki, Pawe?;Wińska, Patrycja;Bretner, Maria;Gizińska, Ma?gorzata;Koronkiewicz, Miros?awa;Staniszewska, Monika [European Journal of Medicinal Chemistry,2018,vol. 150,p. 307 - 333]

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