Procedure:  50 mL 1-neck flask, stirbar, septum, N₂ inlet

                  Dissolved 2.811 g of I and 3.00 mL of Et₃N in 25 mL of dry CH₂Cl₂.  Stirred at 0 C.  Added 1.20 mL of MsCl dropwise (Caution: exotherm).  Stirred for 3 h as bath slowly warmed to rt.  TLC (30:70 EtOAc-hexanes, UV) showed product spot at the same Rf (0.45) as I.  The reaction mixture was poured into ~75 mL of water.  The layers were separated and the organic layer was washed with sat. aq. NH₄Cl followed by sat. aq. NaHCO₃.  The organic layer was dried over MgSO₄ and filtered.  The filtrate was treated with decolorizing carbon, filtered through a plug of silica gel and the solvent was removed by rotary evaporation.  The product was a clear, pale yellow oil and was sufficiently pure at this stage. 

 

¹H NMR (CDCl₃, 400 MHz) d 7.56-7.43 (m, ArH), 4.45 (t, J = 6.8 Hz, CH₂), 3.13 (t, J = 6.8 Hz, CH₂), 2.91 (s, SO₂CH₃).