Diisobutylaluminum hydride → HCID 68524298, compound

Temperature

-50 °C

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.

1. customThe reaction was quenched with an aqueous solution of Rochelle's salt and EtOAc
2. stirringAfter stirring vigorously at rt for 1 h
3. customthe layers separated
4. extractionThe aqueous layer was extracted with EtOAc
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo

ORD record

ord-5e1fd227464343ccb0c6a2206d33c583

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076359B2