Methyl iodide → Ethyl 4-(1,3-dioxoisoindolin-2-yl)-1-methylcyclohexanecarboxylate

Participants

Reaction Steps

A solution of ethyl 4-(1,3-dioxoisoindolin-2-yl)cyclohexanecarboxylate (0.30 g, 1.00 mmol) in THF (10 mL) was cooled to −78° C. followed by dropwise addition of LDA (1.60 M in THF, 1.88 mL, 3.00 mmol) at −78° C. The mixture was stirred at the same temperature for 30 minutes followed by addition of MeI (0.311 mL, 5.00 mmol) at −78° C. The temperature of the reaction was slowly raised up to rt and left to stir overnight. The reaction was then cooled to 0° C. and quenched by dropwise addition of saturated NH4Cl solution (30 mL), extracted with EtOAc (3×50 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product as a viscous liquid (0.30 g, 97%). MS: 316.12 [M+H]+.

Provenance & Evidence