반응 #216721

반응 방정식

2-cyclododecylethyl isocyanate

tetronic acid

triethylamine

KBr

→

4-Hydroxy-2-oxo-2,5-dihydro-furan-3-carboxylic acid-2-cyclododecyl-ethylamide

용매

chloroform

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with 1N HCl
2. 2
   기타the layers separated
3. 3
   건조the organic fraction dried over MgSO4
4. 4
   여과filtered
5. 5
   기타chromatographed
6. 6
   기타to give a yellow solid

실험 절차

To a dry flask containing 40 mL of chloroform was added 1.87 g (18.7 mmol) of tetronic acid, 2.29 g (18.7 mmol) of 4-N,N-dimethylaminopyridine, 2.6 mL (18.7 mmol) of triethylamine followed by 4.4 g (18.7 mmol) of 2-cyclododecylethyl isocyanate. The reaction mixture was allowed to stir overnight at room temperature, after which time a small amount of starting materials was still evident by TLC. The reaction mixture was quenched with 1N HCl, the layers separated, the organic fraction dried over MgSO4, filtered, and stripped of solvent. The residue was flash chromatographed using acidic silica gel eluting with 25% EtOAc/hexane to give a yellow solid. M.P. 135°-137° C. Spectral data follow: 1H NMR (DMSO-d6) δ 8.05 (bs, 1H), 4.6 (s, 2H), 4.2 (bs, 10 H), 3.25 (t, 2H), 2.5 (s, 3H), 1.2-1.4 (bm,>20 H); IR (KBr) 3340, 2920, 2850 (C-H), 1750, 1650 cm-1 (C=O).

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