Ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate → 4-(Trifluoromethyl)-7-(benzyloxy)-1H-indole-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:27]([O-])=O)=[C:11]([CH2:19][C:20](=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[C:11]2[C:10]=1[NH:27][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Procedure
The reaction was carried out in a manner similar to Reference Example 12 c) except for using 10.9 g (26.7 mmol) of ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate, 165 g (213 mmol) of 20% titanium chloride aqueous solution and 100 ml of ethanol. Ethyl 7-benzyloxy-4-trifluoromethyl-2-indolecarboxylate was thus obtained in the yield of 8.00 g (82.6%).