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In a 500 mL round-bottomed flask was cholesteryl tosylate (10.0 g, 18.5 mmol) and 1,10-Decanediol (48.3 g, 277 mmol) suspended in Dioxane (200 ml) to give a white suspension. The flask was fitted with a temperature sensor and reflux condenser. The mixture was heated to reflux and allowed to stir at reflux overnight. The reaction mixture was cooled to room temperature and the solids were filtered off. The solution was concentrated in vacuo. The mixture was re-dissolved in methanol (250 mL) and water (ca. 40 mL) was added to precipitate out the crude product. The precipitate was filtered and dried in vacuo. The residue was further purified via column chromatography on a 100 g Biotage SNAP column eluting over 2 L of a 0-25% EtOAc in Hexanes gradient. Pure fractions were combined and concentrated to give 7.85 g (82%) of a white solid. 1H NMR (300 mHz, CDCl3) δ0.69 (3H, s); 0.85-1.66 (50H, m); 1.75-2.09 (5H, m); 2.14-2.29 (1H, m); 2.32-2.43 (1H, m); 3.14 (1H, tt, J=11.2, 4.4 Hz); 3.46 (2H, dt, J=6.9, 0.4 Hz); 3.65 (2H, t, J=6.6 Hz); 5.36 (1H, d, J=5.3 Hz).

1. customIn a 500 mL round-bottomed flask was
2. customto give a white suspension
3. customThe flask was fitted with a temperature sensor
4. temperaturereflux condenser
5. temperatureThe mixture was heated
6. temperatureto reflux
7. temperatureat reflux overnight
8. filtrationthe solids were filtered off
9. concentrationThe solution was concentrated in vacuo
10. dissolutionThe mixture was re-dissolved in methanol (250 mL)
11. additionwater (ca. 40 mL) was added
12. customto precipitate out the crude product
13. filtrationThe precipitate was filtered
14. customdried in vacuo
15. customThe residue was further purified via column chromatography on a 100 g Biotage SNAP column
16. washeluting over 2 L of a 0-25% EtOAc in Hexanes gradient
17. concentrationconcentrated