ethyl 2-(1-methyl-6,7-dihydro-1H-indol-4(5H)-ylidene)acetate → ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetate
Reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]=2[CH:4]=[CH:3]1>[Pd].CCO>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]=2[CH:4]=[CH:3]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Pd—C (1.3 g, 5%) is added to a solution of a mixture of E/Z isomers of ethyl 2-(1-methyl-6,7-dihydro-1H-indol-4(5H)-ylidene)acetate (3.4 g, 15.50 mmoles) in 100 mL de EtOH, and the resulting solution is stirred under hydrogen atmosphere (25 psi) in a Parr hydrogenator for 8 hours. The reaction mixture is purged with nitrogen, filtered through Celite and the solvent is evaporated under reduced pressure to obtain ethyl 2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)acetate (3.4 g, 15.36 mmol, 99%, oil).