6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol → 6-((tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuro[3,2-b]furan-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-((tetrahydro-2H-pyran-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (5.0 g, 21.7 mmol) in DCM (150 mL) was added DMP (18.4 g, 43.5 mmol) at rt, and then the mixture was stirred at 30° C. overnight and concentrated in vacuo. The residue was dissolved in water (150 mL), and extracted with EtOAc (150 mL×3). The combined organic phases were washed with brine (300 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v)=2/1) to give the title compound as yellow oil (4.96 g, 98%).

Provenance & Evidence