Abstract
The selective and efficient acetylation of the hemiacetal hydroxyl in the equilibrium mixture between RCl2C(OAll)OH and AllOH/RCl2CHO was achieved using the acylating system Ac2O/Et3N/dimethylaminopyridine (DMAP).
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ACKNOWLEDGMENT
We thank the Ministero della Istruzione, dell'Università e della Ricerca (MIUR), for financial assistance.
Notes
a 4 (0.875 mol), 5 (0.875 mol), Et3N (1.013 mol), AcCl (0.875 mol), CH2Cl2 (350 mL), T = −13 °C (2 h) → 0 °C (20 h).
b Yields determined on isolated material.
a 4 (0.2 mol), 5 (0.2 mol), Et3N (0.22 mol), Ac2O (0.2 mol), DMAP (0.02 mol), CH2Cl2 (70 mL), T = −13 °C (2 h) → 0 °C (20 h).
b Yields determined on isolated material.
c In parentheses, the yield observed when using AcCl (Table 1).
d The reaction time at 0 °C is 46 h.