Water → 2-(6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl)isoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate (10.24 g, 34.1 mmol) in DMSO (60 mL) was added (1,3-dioxoisoindolin-2-yl)potassium (8.21 g, 44.3 mmol). The mixture was stirred under N2 atmosphere at 130° C. overnight then cooled down to room temperature, and poured into water. The resulting mixture was extracted with CH2C12 (300 mL×3), and the combined organic layers were washed with water (100 mL×3), dried over Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/1) to afford the title compound as a white solid (2.35 g, 25.0%).

Provenance & Evidence