반응 #42599

반응 방정식

Diethyl malonate

2-propylcyclohexenone

hydrochloric acid

→

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

수율 78.3%

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   추출extracted several times with diethyl ether
2. 2
   세척The combined ether extracts were washed with water, and saturated sodium chloride
3. 3
   건조dried (sodium sulfate)
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타to yield a yellow oil
7. 7
   기타Purification by flash column chromatography (silica, 83:17 hexanes/ethyl acetate)

실험 절차

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).

출처