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To a solution of the (R)-(tetrahydrofuran-2-yl)methanol (Aldrich, 12 g, 0.12 mol) in 40 mL CH2Cl2 and 40 mL pyridine was added 4-dimethylaminopyridine (DMAP, 0.72 g, 5.9 mmol). This mixture was cooled to 0° C. and p-toluenesulfonyl chloride (23.5 g, 0.123 mol) was added portionwise over 20 minutes. The mixture stirred at ambient temperature for 16 hours, then quenched with excess 5% aqueous HCl. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification by column chromatography (SiO2, 65% hexanes in EtOAc) provided the title compound. MS (DCI/NH3) m/z 257 (M+H)+; m/z 274 (M+NH4)+.

1. customquenched with excess 5% aqueous HCl
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification by column chromatography (SiO2, 65% hexanes in EtOAc)