Реакция #42599

Уравнение реакции

Diethyl malonate

2-propylcyclohexenone

hydrochloric acid

→

2-(3-oxo-4-propylcyclohexyl)-malonic acid diethyl ester

Выход 78.3%

Растворители

ethanol

ethanol

Условия реакции

Обработка

1. 1
   Экстракцияextracted several times with diethyl ether
2. 2
   ПромывкаThe combined ether extracts were washed with water, and saturated sodium chloride
3. 3
   Сушкаdried (sodium sulfate)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   Другоеto yield a yellow oil
7. 7
   ДругоеPurification by flash column chromatography (silica, 83:17 hexanes/ethyl acetate)

Методика

A solution of sodium metal (30 mg, 1.30 mmol) in absolute ethanol (4.0 mL) was stirred at −10° C. for 0.5 h. Diethyl malonate (3.5 mL, 23 mmol) was added at −10° C. followed by addition of a solution of 2-propylcyclohexenone (3.0 g, 21.7 mmol) in absolute ethanol (3.0 mL). The reaction mixture was stirred an additional 12 h at room temperature. The reaction mixture was acidified to pH 3 with 10% hydrochloric acid and then extracted several times with diethyl ether. The combined ether extracts were washed with water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to yield a yellow oil. Purification by flash column chromatography (silica, 83:17 hexanes/ethyl acetate) gave 2-(3-oxo-4-propylcyclohexyl)-malonic acid diethyl ester (5.07 g): 1H NMR (300 MHz, CDCl3) δ 4.21 (q, J=7 Hz, 2H), 4.20 (q, J=7 Hz, 2H), 3.30 (s, 0.5H), 3.28 (s, 0.5H), 2.67-1.55 (m, 8H), 1.43-1.11 (m, 10H), 0.90 (t, J=7 Hz, 1.5H), 0.90 (t, J=7.0 Hz, 1.5H).

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