반응 #629597

반응 방정식

2-(3-bromopropyl)benzyl bromide

diethyl acetamidomalonate

→

Ethyl 3-[2-(3-bromopropyl)phenyl]-2-acetamido-2-carboethoxypropanoate

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   온도at reflux under nitrogen for 2 h
2. 2
   온도cooled to 0°-10° C. on an ice bath
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 2 h at 0°-10° C.
4. 4
   기타24 h
5. 5
   기타at room temperature
6. 6
   기타The precipitated inorganic salt was removed by filtration
7. 7
   세척was washed with 20 mL of ethanol
8. 8
   기타The combined solvents were removed under reduced pressure
9. 9
   기타yielding an orange colored oil
10. 10
    기타This oil was chromatographed on a column of silica gel with hexane-ethyl acetate (3:1) as eluant
11. 11
    농축The combined fractions were concentrated under reduced pressure
12. 12
    기타to yield an oil which

실험 절차

To a stirred solution of 0.61 g (27 mmol) Na in 40 mL of dry ethanol was added portionwise 5.86 g (27 mmol) of solid diethyl acetamidomalonate. This mixture was stirred at reflux under nitrogen for 2 h, then cooled to 0°-10° C. on an ice bath. Then, 8.0 g (27 mmol) of 2-(3-bromopropyl)benzyl bromide in 40 mL of dry ethanol was rapidly added. The reaction mixture was stirred for 2 h at 0°-10° C., then 24 h at room temperature. The precipitated inorganic salt was removed by filtration, and was washed with 20 mL of ethanol and discarded. The combined solvents were removed under reduced pressure yielding an orange colored oil. This oil was chromatographed on a column of silica gel with hexane-ethyl acetate (3:1) as eluant. The combined fractions were concentrated under reduced pressure to yield an oil which solidified upon standing, yield 9.5 g (82%), mp 73°-74.5° C. IR(nujol): 1745, 1648 cm-1 (C=O). 1H NMR(D2O) δ 1.3 (t, 6H); 1.9-2.4 (m, 5H); 2.7 (t, 2H); 3.4 (t, 2H); 3.75 (5, 2); 4.3 (q, 4); 6.6 (s, 1H); 7.0-7.3 (m, 4H). Anal Calcd. for C19H26NO3Br: C, 53.28; H, 6.12; N, 3.27; Br, 18.66. Found: C, 53.33; H, 6.13; N, 3.23; Br, 18.67.

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