[NH2-].[Li+].[Li].N.[CH3:5][O:6][CH:7]([O:15][CH3:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[CH:14].C[O:18][CH:19](OC)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]I>CS(C)=O>[CH3:16][O:15][CH:7]([O:6][CH3:5])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=[O:18]
To a stirred suspension of lithium amide, prepared from 1.45 g (0.21 atom) of lithium in ca. 200 ml of liquid ammonia was added 30.6 g (0.18 Mole) of 1,1-dimethoxy-oct-7-yne over a period of 10 min. Dimethyl-sulfoxide (100 ml) was then added, followed by 62.5 g (0.23 Mole) of 1,1-dimethoxy-6-iodohexane within 10 min. Work-up as above gave an oil, from which low-boiling impurities were removed by heating at 100°/0.05 Torr. Crude tetradec-7-yn-1,14-dial dimethylacetal (40.8 g, 72% yield) was used without further purification. A sample was submitted to a rapid distillation: b.p. 140°/0.05 Torr.--IR: 1125, 1070, 1050 cm-1.
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