1-Dodecanethiol → HCID 59590777, compound

Participants

Reaction Conditions

Reaction Steps

A screw-cap vial was charged with 42.2 (0.195 g, 0.832 mmol), NMP (0.8 mL), sodium hydroxide (0.150 g, 3.75 mmol), and 1-dodecanethiol (available from Aldrich) (0.699 mL, 2.91 mmol). The mixture was stirred overnight at 125° C. (sealed vial) and cooled to room temperature. Additional NMP (0.8 mL), sodium hydroxide (0.150 g, 3.75 mmol), and 1-dodecanethiol (0.699 mL, 2.91 mmol) were added, and the mixture was stirred for 72 hours at 125° C. and cooled to room temperature. The solidified mixture was fractured with a spatula, diluted with 1 N HCl, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (20-50% EtOAc/hexanes) to afford 42.3 (0.119 g, 65% yield) as a brown oil.

Provenance & Evidence