تفاعل #218299

معادلة التفاعل

sodium hydride

diethyl malonate

5-bromo-1-pentene

→

oil

المردود 101.1%

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

المردود 101.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was warmed to rt
2. 2
   أخرىpartitioned between ether and water
3. 3
   أخرىThe layers were separated
4. 4
   استخلاصthe aqueous layer was extracted with ether (2×250 mL)
5. 5
   غسيلthe combined organic phases were washed with water (2×) and brine
6. 6
   تجفيفdried over MgSO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

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).

المصدر