반응 #216718

반응 방정식

1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride

KBr

tetronic acid

dimethylaminopyridine

3-cyclohexylpropanoic acid

→

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

용매

N,N-dimethylformamide

triethylamine

반응 조건

후처리

1. 1
   기타After 10 minutes the ice bath is removed
2. 2
   workup.STIRRINGto stir overnight
3. 3
   기타The reaction mixture is quenched with 1N hydrochloric acid
4. 4
   세척the solution is washed 3 times with hexanes
5. 5
   세척washed with brine
6. 6
   건조dried over magnesium sulfate
7. 7
   기타evaporated
8. 8
   기타to give a yellow solid, which
9. 9
   기타is recrystallized from hexanes
10. 10
    기타to give light yellow crystals

실험 절차

To a solution of 2.0 g of tetronic acid in 40 ml of dry N,N-dimethylformamide was added (at 0° C.) 3.1 ml of triethylamine and 0.81 g of dimethylaminopyridine. After stirring for 5 minutes, 3.4 ml of 3-cyclohexylpropanoic acid was added, followed by 4.6 g of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride. After 10 minutes the ice bath is removed and the mixture is allowed to stir overnight. The reaction mixture is quenched with 1N hydrochloric acid and the solution is washed 3 times with hexanes. The combined organic layers are combined, washed with brine, dried over magnesium sulfate and evaporated to give a yellow solid, which is recrystallized from hexanes to give light yellow crystals: m.p. 75°-78° C.; IR (KBr) 2910, 2820, 1750, 1640, 1600 cm-1 ; NMR (CDCl3) δ 0.9-1.8 (1 1H, m), 2.9 (t, 2H, J=6 Hz), 4.7 and 4.5 (s, 2H (tautomers)); MS EI M+ 238.

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