Methanesulfonic Acid → Hexahydrofuro(2,3-b)furan-3-ol

Participants

Reaction Conditions

Reaction Steps

In a 50 mL round bottom flask, 1-(2-iso-propoxytetrahydro-3-furanyl)-1,2-ethanediol (2.21 g; 8.89 mmoles, 1 eq.) was dissolved in tetrahydrofuran (9 mL). After cooling at 0° C., methanesulfonic Acid (65 mg; 676.33 mmoles) was added to the mixture. The reaction mixture was thereafter heated at 45° C. for 30 min. After cooling at room temperature, triethylamine (0.3 g; 2.96 mmoles) was added to the mixture. The solvent was evaporated and ethyl acetate (9 mL; 91.98 mmoles) was added to the mixture at room temperature. Then the mixture was filtered over dicalite and the solvent was evaporated under reduced pressure to afford endo/exo bis-THF (1.562 g; GC: 71 area %) in a diastereomeric ratio of 15/85 endo/exo diastereoisomers.

Provenance & Evidence