反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A mixture of 10.30 g (1.1 eq) of 80% sodium hydride in mineral oil is washed twice with anhydrous tetrahydrofuran (to remove the mineral oil) and 400 mL of tetrahydrofuran are then added. This is cooled to 0° C. and a solution of 35.29 g (1.0 eq) of ethyl cyanoacetate in anhydrous tetrahydrofuran is added dropwise under nitrogen. The mixture is stirred vigorously at ambient temperatures until the evolution of hydrogen ceases and an anhydrous solution of 89.33 g (1.0 eq) of methyl 4-(4-mesitylbutyl)benzoate is then added in a dropwise fashion. The mixture is stirred at ambient temperatures for 12 hours, then at reflux temperatures for 6 hours, and then cooled. The solvent is removed under reduced pressure and diethyl ether is added. The organic phase is separated, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The residue is chromatographed with 1:4 ethyl acetate:hexane and the homogeneous fractions are combined and concentrated to yield methyl 4-(5-carboethoxy-5-cyanopentyl)benzoate as a liquid, IR (film) vmax 2915, 2860, 2255, 1730, 1609, 1571, 1432, 1413, 1368, 1320, 1178, 1105, 1019, 962, 853, 759, and 602 cm-1 ; 1H NMR (CDCl3) delta 7.95 (d, J=8.1 Hz, 2H, Ar), 7.24 (d, J=8.1 Hz, 2H, Ar), 4.25 (q, J=7.2 Hz, 2H, CH2CH3), 3.90 (s, 3H, CO2CH3), 3.46 (t, J=6.8 Hz, 1H, CHCN), 2.69 (t, J=7.5 Hz, 2H, benzyl), 1.93-2.00 (m, 2H, CH2CH), 1.54-1.72 (m, 4H, 2° aliphatic), 1.30 (t, J=7.3 Hz, 3H, CH2CH3).
WORKUP
后处理
- washis washed twice with anhydrous tetrahydrofuran (
- customto remove the mineral oil) and 400 mL of tetrahydrofuran
- additionare then added
- temperatureat reflux temperatures for 6 hours
- temperaturecooled
- customThe solvent is removed under reduced pressure and diethyl ether
- additionis added
- customThe organic phase is separated
- washwashed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue is chromatographed with 1:4 ethyl acetate
- concentrationconcentrated