May 1967
S-AZA
Iv
4; 1
nient, Wyeth Laboratories Inc. , for obtaiiiiiig aiid discussing the biological data, and Dr. Iean-St~arktrap for 4 hr. The sollition was cooled and washed with K X 0 3 solution and water. The benzene layer wa3 dried and concentrated to 3.9 g of heavy oil which crystallized. The ketal (15d, transparent in the C=O region of the infrared) was dissolved in 50 ml each of dry THF and t-butyl alcohol and added to ca. 400 ml of liquid NH,. Lithium (3.5 g) was added in small pieces over a 20-min period, and the blue solution was stirred for 1..5 hr a t reflux. Ethanol was added dropwise to discharge the bliie color, and the NHI was allowed to evaporate. Water (100 ml) was added, and t.he TIIF was removed by distillation. The mixture was extracted with ethyl wetate, and the organic phase was dried and concentrated to give ;.;.4 g of white solid enol ether keial a.hii~hshowcd etid absorption
