Реакция #91076

Уравнение реакции

ethyl 2-oxocyclopentanecarboxylate

ethyl 2-bromoacetate

K2CO3

→

title compound

Выход 37.8%

Ethyl 1-(2-Ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate

Выход 37.8%

Растворители

acetone

Условия реакции

Обработка

1. 1
   ФильтрацияThe solid was filtered off
2. 2
   Промывкаthe filter cake was washed with acetone (3×100 mL)
3. 3
   КонцентрированиеThe filtrate was concentrated
4. 4
   Другоеthe resultant liquid was purified by a silica gel plug

Методика

To a solution of ethyl 2-oxocyclopentanecarboxylate (93.27 g, 597 mmol) and ethyl 2-bromoacetate (144.64 g, 866 mmol) in acetone (1.2 L) was added K2CO3 (165 g, 1194 mmol). The mixture was heated at 56° C. for 24 h. The solid was filtered off and the filter cake was washed with acetone (3×100 mL). The filtrate was concentrated and the resultant liquid was purified by a silica gel plug to give the title compound as light yellow liquid (54.7 g). LCMS m/z=243.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (t, J=7.14 Hz, 3H), 1.24 (t, J=7.14 Hz, 3H), 1.95-2.03 (m, 1H), 2.06-2.15 (m, 2H), 2.35-2.50 (m, 2H), 2.55-2.60 (m, 1H), 2.80 (dd, J=15.2, 2.09 Hz, 1H), 2.95 (dd, J=15.2, 2.09 Hz, 1H), 4.09 (q, J=7.14 Hz, 2H), 4.12 (q, J=7.14 Hz, 2H).

Источник