反应 #65579

反应方程式

3-cyclododecylpropanoic acid

KBr

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

tetronic acid

triethylamine

dimethylaminopyridine

→

3-(3-Cyclododecyl-1-oxopropyl)-4-hydroxy-2(5H)-furanone

溶剂

hexane ethyl acetate

dimethylformamide

反应条件

后处理

1. 1
   其他After 10 minutes the ice bath is removed
2. 2
   workup.STIRRINGto stir overnight at room temperature
3. 3
   workup.ADDITIONThe reaction mixture is then poured into 1.0N hydrochloric acid
4. 4
   萃取extracted 3 times with ethyl acetate
5. 5
   洗涤washed with brine
6. 6
   干燥dried over magnesuim sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated
9. 9
   其他to give a yellow oil
10. 10
    其他to give an off white solid

实验过程

To a solution of 0.70 g (7 mmol) of tetronic acid in 20 ml of dry dimethylformamide at 0° C. is added 1.1 ml (836 mg, 8.3 mmol) of triethylamine and 0.31 g (2.5 mmol) of dimethylaminopyridine. After stirring for 5 minutes, 2.0 g (8.3 mmol) of 3-cyclododecylpropanoic acid is added followed by 1.6 g (8.3 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. After 10 minutes the ice bath is removed and the reaction mixture is allowed to stir overnight at room temperature. The reaction mixture is then poured into 1.0N hydrochloric acid and extracted 3 times with ethyl acetate. The organic layers are combined, washed with brine, dried over magnesuim sulfate, filtered and concentrated to give a yellow oil. The oil is subjected to flash chromatography using acidic silica gel and hexane/ethyl acetate (3:2) as the mobile phase to give an off white solid: m.p. 99°-102° C.; IR (KBr) 2940, 1710, 1600 and 1470 cm-1 ; NMR (CDCl3) (mixture of tautomeric forms) δ 1.34 (mc, 22H), 1.50 (bs, 1H), 1.61 (m, 2H), 2.92 (m, 2H), 4.55 and 4.70 (s, 2H); MS (EI)

来源