Sodium Acetate → 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 (Ketone 2) in a mixture of toluene (300 mL) and HOAc (150 mL) was added NaOAc (15 g) and 1-(4-methoxyphenyl)-1-(4-chlorobenzyl)-hydrazine hydrochloride (50 g). The reaction was stirred at r.t. for 3 days under argon in the dark. The mixture was poured onto H2O (1 L) and extracted with 3× EtOAc (500 mL). The EtOAc was washed with 3× H2O (500 mL) 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