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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; [ a I z 3 D -52' ( c 5, MeOH); 13C NMR and mass spectra were identical with those of 11.

the journal of organic chemistry

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