Tetrahydrofuran → Methyl Myristate

Temperatur

0 °C

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.

1. temperaturewarmed to room temperature
2. stirringstirred an additional 4 h
3. customThe reaction was quenched by addition of diethyl ether
4. washwashing with sat'd aq. NaHCO3
5. washby washing with brine
6. customThe organic layer was separated
7. dry with materialdried (Na2SO4)
8. customThe solvents were removed by rotary evaporation
9. customthe crude product was purified by silica gel column chromatography

ORD-Eintrag

ord-7aa3d9d46bf042f4823b7431f3d92986

Quelldatensatz

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06200599B1