Ethylene Glycol → HCID 68461234, compound

Temperature

60 °C

Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL) (caution: exotherm). m-Methoxybenzyl chloride (0.21 mL, 1.5 mmol) was added to the reaction, and the residual m-methoxybenzyl chloride was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) was then added, and the reaction was heated at 60° C. for 18 h and then cooled to room temperature for 4 h. H2O (2 mL) and EtOAc (2 mL) were added, and the layers were separated via pipette. The aqueous layer was extracted with EtOAc (1×1 mL), and the combined organic layers were concentrated. The crude product was purified on a Biotage 12+M cartridge (8 g silica) eluting with 30% EtOAc/hexanes at 5 mL/min to give the title compound (114 mg, 42%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

1. temperaturecooled to room temperature for 4 h
2. customthe layers were separated via pipette
3. extractionThe aqueous layer was extracted with EtOAc (1×1 mL)
4. concentrationthe combined organic layers were concentrated
5. customThe crude product was purified on a Biotage 12+M cartridge (8 g silica)
6. washeluting with 30% EtOAc/hexanes at 5 mL/min

ORD record

ord-ef7713b5bb9e47f88109c40a150bb0c6

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309572B2