Tetrahydrofuran → Methyl Myristate

Participants

Reaction Conditions

Reaction Steps

Oxetane 2 (5 g, 41 mmol) was dried in vacuo at 100° C. for 1 h and then dissolved in THF (120 mL). To the solution at room temperature was added freshly distilled triethylamine (10 mL, 72 mmol) and N,N-(dimethylamino)pyridine (400 mg, 3.3 mmol) and the reaction was cooled to 0° C. Myristoyl chloride (8.9 mL, 33 mmol) was added via cannula to the reaction mixture, and the resulting yellowish solution was stirred at 0° C. for 4 h and then warmed to room temperature and stirred an additional 4 h. The reaction was quenched by addition of diethyl ether and washing with sat'd aq. NaHCO3, followed by washing with brine. The organic layer was separated and dried (Na2SO4). The solvents were removed by rotary evaporation, and the crude product was purified by silica gel column chromatography to yield 8 g (74%) of the ester 3 as white powder.

Provenance & Evidence