Levulinic Acid → Indole

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Cl.F[C:3]1[CH:4]=[C:5]([NH:11]N)[C:6](OC)=[CH:7][CH:8]=1.[C:13](O)(=O)[CH2:14]CC(C)=O>C(O)(=O)C>[NH:11]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:3][CH:4]=2)[CH:14]=[CH:13]1

참가 물질

실험 절차

Condensation of hydrazine hydrochloride (2) with levulinic acid (3) in acetic acid results in the formation of two regioisomeric indole derivatives 4 and 5 in a 1:7 ratio. The major regioisomer 5 can be isolated in pure form by crystallization of the reaction mixture. Alternatively, the indole mixture can be esterified with an alcohol such as 2-trimethylsilylethanol to afford the corresponding esters that can then be separated by a number of means, for example by chromatography.