تفاعل #65579

معادلة التفاعل

3-cyclododecylpropanoic acid

KBr

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

tetronic acid

triethylamine

dimethylaminopyridine

→

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

المذيبات

hexane ethyl acetate

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter 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
   استخلاصextracted 3 times with ethyl acetate
5. 5
   غسيلwashed with brine
6. 6
   تجفيفdried over magnesuim sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىto give a yellow oil
10. 10
    أخرىto give an off white solid

الإجراء التجريبي

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)

المصدر