Water → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

Participants

Reaction Steps

To a solution of 39 g methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate in a mixture of 300 mL toluene and 150 mL glacial HOAc acid was added 15 g NaOAc and 50 g 1-(4-methoxyphenyl)-1-(4-chlorobenzyl)hydrazine hydrochloride. The reaction was stirred at room temperature for 3 days under argon in the dark. The mixture was poured onto H2O (1L) and extracted with 3×500 mL EtOAc. The EtOAc was washed with 3×500 mL H2O then once with NaHCO3 solution. The organic phase was dried (MgSO4), evaporated to dryness and the residue crystallised from Et2O/hexane 2:1 to afford the title compound, m.p. 102°-103° C.

Provenance & Evidence