3,4-dihydro-2H-pyran → 2-(Oxan-2-yloxy)isoindole-1,3-dione

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Reaction Steps

to a vigorously stirred solution of N-hydroxyphthalimide (10.0 g, 61.4 mmol) in CH2Cl2 (70 mL) and dioxane (80 mL) was added dihydropyran (6.16 mL, 67.6 mmol) and p-toluenesulfonic acid (200 mg). The resulting solution was stirred overnight at room temperature. The reaction was quenched by slow addition of saturated NaHCO3 (100 mL). After separation, the organic layer was washed with brine and dried over Na2SO4. Solvent removal under vacuum yielded 13.4 g (88%) of 2-(tetrahydro-2H-pyran-2-yloxy)isoindoline-1,3-dione as a white solid.

Provenance & Evidence