반응 #216719

반응 방정식

dimethylaminopyridine

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

tetronic acid

triethylamine

4-cyclohexyl butyric acid

→

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

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITAfter 10 minutes
2. 2
   기타the ice bath is removed
3. 3
   workup.STIRRINGto stir overnight
4. 4
   기타The reaction mixture is quenched with 1N HCl
5. 5
   세척the solution is washed three times with hexanes
6. 6
   세척The combined organic layers are washed with water
7. 7
   건조dried over magnesium sulfate
8. 8
   기타evaporated
9. 9
   기타chromatographed on silica gel using 5% methanol/ethyl acetate with 2 mL of acetic acid/liter
10. 10
    기타to give an orange solid

실험 절차

To a solution of 1.0 g (10.0 mmol) of tetronic acid in 30 mL of dry N,N-dimethylformamide at 0° C. is added 1.5 mL (11 mmol) of triethylamine followed by 0.37 g (30 mmol) of 4 dimethylaminopyridine. After stirring at 0° C. for 5 minutes, 2.0 g (11.7 mmol) of 4-cyclohexyl butyric acid is added, followed by 2.25 g (11.7 mmol) of 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide. After 10 minutes, the ice bath is removed and the reaction mixture is allowed to stir overnight. The reaction mixture is quenched with 1N HCl and the solution is washed three times with hexanes. The combined organic layers are washed with water, dried over magnesium sulfate and evaporated. The residue is flash chromatographed on silica gel using 5% methanol/ethyl acetate with 2 mL of acetic acid/liter to give an orange solid: m.p. 38-42° C.; IR (film) 2920, 2840, 1770, 1690, 1660, 1600 cm-1 ; NMR (CDCl3) δ 0.9 (m, 2H), 1.2 (m, 6H), 1.7 (m, 6H), 2.9 (q, J=7 Hz, 2H), 4.6 and 4.7 (s, 2H), 12.1 (bs, 1H); MS (EI): M+ 252.

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