CO[CH:3]=[CH:4][C:5](=[O:7])[CH3:6].[C:8]([O-])([O-])=[O:9].[K+].[K+].CO.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][SH:20]>O1CCCC1.CCOCC.O>[CH3:16][O:17][C:18]([O:9][CH3:8])([O:21][CH3:22])[CH2:19][S:20][CH2:3][CH2:4][C:5](=[O:7])[CH3:6]To a solution of 2.3 g. (18.9 mmol) of 4-methoxy-3-buten-2-one and 50 mg. K2CO3 in 15 ml. of methanol was added 1.88 g. (18.9 mmol) of 2-mercaptoacetaldehyde dimethyl acetal and the reaction mixture heated to reflux for 10 minutes. On cooling, the methanol was removed by rotatory evaporation, 25 ml. of ether was added and the solution was extracted with water, brine, and dried over anhydrous magnesium sulfate. Filtration and removal of solvent afforded 2.95 g. (70%) of water white oil homogeneous by TLC (SiO2), tetrahydrofuran/ether, 1:1; Mol. dist. 140° (0.2 mm Hg), 1H-NMR (CDCl3) delta 2.21 (s, 3), 2.66-3.11 (m, 4), 3.42 (s, 9), 4.44 (t, 1), 4.89 (doublet of doublets, 1); IR (film) cm-1 1710 (s).
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