Ethylene Glycol → HCID 68461234, compound

Participants

Reaction Conditions

Reaction Steps

Ethylene glycol (0.084 mL, 1.51 mmol) was added to NaH (38 mg, 1.5 mmol, 95% in oil) in THF (3 mL). 3-(Chloromethyl)phenyl methyl ether (0.21 mL, 1.5 mmol) was added to the reaction, and the residual 3-(Chloromethyl)phenyl methyl ether 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 rt 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 by flash chromatography eluting with 30% EtOAc/hexanes at 5 mL/min (10 mL) to give the title compound (114 mg, 42%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

Provenance & Evidence