C([Li])CCC.[CH2:6]([C:9]12[CH2:16][S:15][CH:12]([S:13][CH2:14]1)[S:11][CH2:10]2)[CH2:7][CH3:8].Cl[CH2:18][O:19][CH2:20][CH2:21][C:22]#[CH:23].O>O1CCCC1>[CH2:20]([O:19][CH2:18][C:12]12[S:11][CH2:10][C:9]([CH2:6][CH2:7][CH3:8])([CH2:16][S:15]1)[CH2:14][S:13]2)[CH2:21][C:22]#[CH:23]n-Butyllithium (0.3 ml,1.6M solution in hexane) was added to a solution of 4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane (0.1 g) in dry tetrahydrofuran (5 ml) at -70°, under nitrogen. The solution was stirred for 30 minutes and but-3-ynyl chloromethyl ether (0.058 g) in dry tetrahydrofuran (2.0 ml) was added and the reaction mixture was allowed to warm to 20°. Water (10 ml) was added and the mixture was extracted with diethyl ether. The ethereal extracts were dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was purified by chromatography on alumina, eluting with 1:10 dichloromethane:hexane saturated with ammonia. 1-(But-3-ynyloxy-methyl)-4-n-propyl-2,6,7-trithiabicyclo[2.2.2]octane was obtained as a waxy solid (0.032 g).
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