[Li].[CH2:2]([O:4][C@@H:5]1[C@:13]2([CH2:14][CH3:15])[C@H:8]([C@@H:9]3[CH2:23][CH2:22][C:21]4[CH:20]=[C:19]([O:24]C)[CH:18]=[CH:17][C:16]=4[C@H:10]3[CH2:11][CH2:12]2)[CH2:7][CH2:6]1)[CH3:3].COCC(O)C.N>COCCOC>[CH2:2]([O:4][C@@H:5]1[C@:13]2([CH2:14][CH3:15])[C@H:8]([C@@H:9]3[CH2:23][CH2:22][C:21]4[C@H:16]([CH2:17][CH2:18][C:19](=[O:24])[CH:20]=4)[C@H:10]3[CH2:11][CH2:12]2)[CH2:7][CH2:6]1)[CH3:3]Add 2.0 g. of lithium to a suspension of 2.0 g. of dl-17β-ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene, 90 ml. of 1,2-dimethoxyethane, 100 ml. of 1-methoxy-2-propanol, and 300 ml. of ammonia while stirring. Treat with 2.0 g. of ammonium chloride and water, filter off the precipitate and add it to 80 ml. of methanol, 4 ml. of water, and 5 ml. of conc. hydrochloric acid. Stir for one hour and dilute with water. Extract the product with ether and recrystallize it successively from methanol-water and petroleum ether-ether to obtain the title substance, m.p. 95°-97°; ultraviolet peak at 244 mμ (15,900); infrared peak at 6.0 μ.
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