Relative reactivities of acetals and orthoesters in Lewis acid catalyzed reactions with vinyl ethers. A systematic investigation of the synthetic potential of acetals and orthoesters in electrophilic alkoxyalkylations of enol ethers

3 h.Workup gave 1.41 g (91%) of recrystallized (CH2C1,/EtOAc) 11: mp 149-150 OC; [ a ] D +51.88' (c 4.8, MeOH); l3C NMR 6 150.00, 140.18, 129.29,129.07,128.58,126.14,123.03,121.32, 117.29, 112.23, 81.83, 56.44, 47.56, 34.20, 33.19; mass spectrum (EI), m / z (relative intensity) 167,44 (loo), 148 (8), (CI) 272 (100, M').Anal.Calcd for C1,HzzC1NO2: C, 66.34; H, 7.15; N, 4.55; C1, 11.5.Found: C, 66.08; H, 5.29; N, 4.66; C1, 11.59. [ S 1-(-)-Chloro-3-phenyl-3-( 2-methoxyphenoxy )propane (8).Chloro ether 8 was prepared by a procedure similar to the one used for 5: yield, 1.64 g (60%); mp 59-61 "C; -41.6' (c 3, CHCI,); 13C NMR and mass spectrum were identical with those of 5. [SI-(-)-Nisoxetine Hydrochloride(14).[SI-(-)-Nisoxetine hydrochloride was prepared by a procedure similar to the one used for 11: yield, 1.41 g (91%); mp 149-151 OC; [aIz3D -52' ( c 5, MeOH); 13C NMR and mass spectra were identical with those of 11.Acknowledgment.We would like t o thank the United States Army Research Office ( D U G 29-82-K-0047) for the financial assistance which made o u r studies possible.Registry No. 1, 100306-34-1; 2, 100306-33-0; 3, 114446-47-8; 4