Procedure:  250 mL 1-neck flask, stirbar, septum, N₂ inlet

                  Prepared a suspension of 1.003 g of NaH in 100 mL of dry THF.  Stirred at rt.  Added 3.087 g of diol I.  Stirred for 2h;  added 6.638 g of carbamyl chloride III.  Let stir overnight.  Quenched with water.  Extract with Et₂O.  The organic layer was dried over MgSO₄, filtered and the solvent was removed by rotary evaporation.  The product was isolated by flash chromatography on silica gel using 40:60 EtOAc-hexanes as eluant.  The product was a clear, colorless oil.  Also collected 2.065 g of the dicarbamate. 

 

¹H NMR (CDCl₃, 300 MHz) d 4.27 (dd(apparent t), J = 5.9 Hz, CH₂OCO), 4.10-3.70 (b, NCH), 3.63 (dt(apparent q), J = 6.1 Hz, CH₂CH₂OCO), 2.79 (t, J = 6.5 Hz, OH), 1.82 (pent., J = 5.9 Hz, HOCH₂), 1.19 (d, J = 6.8 Hz, NCH(CH₃)₂).