C(O[CH:5]1[CH:9]([CH:10]([OH:13])[CH2:11][OH:12])[CH2:8][CH2:7][O:6]1)(C)C.CS(O)(=O)=O.C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1>[O:12]1[CH:5]2[O:6][CH2:7][CH2:8][CH:9]2[CH:10]([OH:13])[CH2:11]1In 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.
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