Diisobutylaluminum hydride → HCID 68524298, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(2-methoxyethoxy)-5-(2-methoxyethyl)benzoate (1 eq.) from the previous step in THF (0.1 M) at −78° C. was added DIBAL-H (3 eq.). The reaction was warmed to −50° C. for 1 h, and then stirred at 0° C. for an additional 30 min. The reaction was quenched with an aqueous solution of Rochelle's salt and EtOAc. After stirring vigorously at rt for 1 h, the layers separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo to give [3-(2-methoxyethoxy)-5-(2-methoxyethyl)phenyl]methanol as an oil. This intermediate (1 eq.) was dissolved in DCM and added to a solution of DMSO (2.5 eq.) and oxalyl chloride (2.5 eq.) in DCM, premixed at −78° C. for 25 min. After 5 min, triethylamine (5 eq.) was added, and the reaction was warmed to rt over 30 min. The reaction was quenched with 1 N aqueous HCl and extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 30% EtOAc in Hex) to give the title compound as an oil.

Provenance & Evidence