Neopentyl alcohol → 2,2-Dimethylpropyl 8-(p-chlorophenyl-sulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Participants

Reaction Steps

To a solution of 0.378 g of 2,2-dimethyl propanol in 3 mL tetrahydrofuran is added 0.003 mL of 2.5 M n-butyllithium in hexane. To this solution is added 0.332 g methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate and the mixture is refluxed for 20 hours. The reaction is quenched by addition of 3 mL of saturated ammonium chloride solution. It is then extracted with methylene chloride (3×10 mL). The combined organic extracts are dried, filtered and evaporated to dryness to give a clear oil which is purified by preparative thin layer chromatography to obtain 2,2-dimethylpropyl 8-(p-chlorophenyl-sulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate as a pale yellow oil.

Provenance & Evidence