Triethylamine → 1,2-Dilinoleyl-3-methanesulfonylglycerol

Participants

Reaction Conditions

Reaction Steps

1,2-Dilinoleylglycerol (26) (11.0 g, 18.7 mmol), triethylamine (5.04 mL, 36 mmol), and a stir bar were added to a 250 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (75 mL) was added, and the mixture cooled to −15° C. (Ice and NaCl). Mesyl Chloride (2.80 mL, 36 mmol) was added via syringe over a 5 minute period, and the reaction stirred at −15° C. for 1 hour. At this point TLC showed that the starting material had been consumed. The solution was diluted with DCM (120 mL) and washed with saturated NaHCO3 (2×150 mL). The organic phase was then dried (MgSO4), filtered, concentrated, and the product purified by column chromatography (10.6 g, 85%).

Provenance & Evidence