Trifluoroacetic acid → 1-[3-(4-Octylphenoxy)-2-oxopropyl]indole-2-carboxylic acid
Reaction equation
C([O:5][C:6]([C:8]1[N:9]([CH2:17][C:18](=[O:35])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:23][CH:22]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][C:18](=[O:35])[CH2:17][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=[C:8]2[C:6]([OH:7])=[O:5])=[CH:26][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]Participants
4
Procedure
0.046 g (0.096 mmol) tert-butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-2-carboxylate is dissolved in 10 ml absolute dichloromethane and mixed with 1.49 g (13.6 mmol) trifluoroacetic acid. Having stirred at room temperature for 1½ hours, concentration to dryness is carried out on the rotary evaporator. Two dissolution steps in toluene and respective concentration on the rotary evaporator leave as a crude product a yellowish solid which is recrystallized from petroleum ether/ethyl acetate (67:33) and yields the product as a white solid.