Ethanol → 4-(furan-2-ylmethoxy)-1H-indole-2-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])C.[OH-].[K+].CCO>>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[CH2:16][O:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]2Participants
4
Procedure
The 4-(furan-2-ylmethoxy)-1H-indole-2-carboxylic acid ethyl ester 94 obtained above is mixed with a 1M-solution of KOH in EtOH (13.3 ml, 13.3 mmol) and stirred for 24 hours. The solvent is then evaporated and the residue is partitioned between water and ether. The water layer is acidified with HCl and extracted twice with EtOAc. The combined organic layers are washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to give a white powder.