Реакция #538256

Уравнение реакции

2-(4-chlorophenyl)cyclopentanone

carbonisocyanatidic chloride

→

7-(4-chlorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione

Выход 51.1%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling to rt
2. 2
   Промывкаwashed with saturated aqueous solution of sodium bicarbonate
3. 3
   ДругоеThe organic layer was separated
4. 4
   Экстракцияthe aqueous layer was extracted twice with ethyl acetate
5. 5
   СушкаThe combined organic extracts were dried over anhydrous sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   ДругоеThe solvent was removed in vacuum
8. 8
   Другоеthe oily residue was purified by column chromatography on silica gel

Методика

A solution of 2-(4-chlorophenyl)cyclopentanone (7.80 g, 40.1 mmol) and carbonisocyanatidic chloride (7.61 g, 72.1 mmol) was stirred at 58° C. in a high-pressure vessel for 1 h. The temperature was raised to 130° C. and the reaction mixture was stirred for an additional 2 h. After cooling to rt, the reaction mixture solidified. The solid residue was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuum and the oily residue was purified by column chromatography on silica gel to provide 7-(4-chlorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (5.4 g, 20.48 mmol, 51.1% yield). LC-MS (M+H)+=264.2. 1H NMR (500 MHz, CDCl3) δ ppm 7.32 (2H, d, J=8.5 Hz), 7.12 (2H, d, J=8.5 Hz), 4.15-4.25 (1H, m), 2.56-2.93 (4H, m).

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