반응 #218299

반응 방정식

sodium hydride

diethyl malonate

5-bromo-1-pentene

→

oil

수율 101.1%

2-Pent-4-enyl-malonic acid diethyl ester

수율 101.1%

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction mixture was warmed to rt
2. 2
   기타partitioned between ether and water
3. 3
   기타The layers were separated
4. 4
   추출the aqueous layer was extracted with ether (2×250 mL)
5. 5
   세척the combined organic phases were washed with water (2×) and brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated

실험 절차

A mixture of sodium hydride (60% in mineral oil, 2.4 g, 60.5 mmol, 1.1 eq) and diethyl malonate (8.34 mL, 55 mmol, 1 eq) in DMF (200 mL) was cooled to 0° C. and 5-bromo-1-pentene (6.5 mL, 55 mmol, 1 eq) was added dropwise. The reaction mixture was warmed to rt, stirred for 14 hours and then partitioned between ether and water. The layers were separated, the aqueous layer was extracted with ether (2×250 mL) and the combined organic phases were washed with water (2×) and brine, dried over MgSO4 and concentrated to give E1.1 as a colorless oil (12.7 g, 100% yield). 1H NMR (400 MHz, CDCl3): δ 5.71 (m, 1 H), 4.92 (m, 2 H), 4.12 (q, J=7.1 Hz, 4 H), 3.25 (t, J=7.58 Hz, 1 H), 2.01 (m, 2 H), 1.83 (m, 2 H), 1.36 (m, 2 H), 1.20 (t, J=7.1 Hz, 6 H).

출처