Ethylene Glycol → 851859-50-2

Temperatur

60 °C

Ethylene glycol (0.1 mL, 1.79 mmol) was added to NaH (46 mg, 1.81 mmol, 95% in oil) in THF (5 mL). 1-(Bromomethyl)-3-fluorobenzene (0.22 mL, 1.79 mmol) was added to the reaction, and the reaction was heated at 60° C. for 5 days. H2O (2 mL) and EtOAc (2 mL) were added, and the layers were separated via pipette. The aqueous layer was extracted with EtOAc (3×1 mL), and the combined organic layers were washed with saturated NaCl (1×2 mL), dried (Na2SO4), and concentrated. The crude product was purified on a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: 30% EtOAc/hexanes (fractions 1,2), 50% EtOAc/hexanes (fraction 3), and 75% EtOAc/hexanes (fraction 4) to give the title compound (76.2 mg, 25%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

1. customthe layers were separated via pipette
2. extractionThe aqueous layer was extracted with EtOAc (3×1 mL)
3. washthe combined organic layers were washed with saturated NaCl (1×2 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customThe crude product was purified on a SPE cartridge (5 g silica)
7. washeluting with the following 10 mL fractions

ORD-Eintrag

ord-b8a32c54b47f40f9ab47bd63ae0432c3

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853404B2