Procedure:  100 mL 1-neck flask, stirbar, septum, N₂ inlet

                  Dissolved 0.471 g of alcohol I in 10 mL of dry THF.  Stirred at rt.  Added 0.459 g of DEAD followed by 0.695 g of Ph₃P and 0.390 g of phthalimide.  After 16 h, TLC (10:90 EtOAc-hexanes, PMA) shows unreacted starting material at Rf 0.35 and product spot at Rf 0.51.  Added an additional 0.088 g of phthalimide, 0.184 g of Ph₃P and 0.144 g of DEAD.  After 5 h, the solvent was removed by rotary evaporation to give a viscous yellow oil.  The product was isolated by flash chromatography on silica gel using 10:90 EtOAc-hexanes as eluant.  The product was a clear, pale yellow oil. 

 

¹H NMR (CDCl₃, 300 MHz) d 7.79 (dd, J = 5.5, 3.1 Hz, ArH), 7.67 (dd, J = 5.5, 3.1 Hz, ArH), 5.69 (m, H2), 5.01 (dd, J = 17.1, 1.4 Hz, trans H1), 4.91 (d, J = 11.0 Hz, cis H1), 4.26 (tt, J = 10.1, 5.3 Hz, H4), 2.78 (m, H3), 2.47 (m, H3), 2.07 (m, H5), 1.71 (m, H5), 1.19 (m, CH₂s), 0.84 (bt, J = 6.8 Hz, CH₃)

 

notes

 

Both cyclic and acyclic imides as well as hydrazoic acid (HN₃) can be alkylated using the Mitsunobu reaction (see Mitsunobu, O. Synthesis 1981, 1).  The reaction generally proceeds with complete inversion of stereochemistry at the alcohol reacting center.