Cl[CH2:2][CH2:3][CH2:4][S:5][CH3:6].[Mg].[CH3:8][S:9][CH2:10][CH2:11][CH:12]=[O:13].[Cl-].[NH4+]>C1COCC1.CCOCC>[CH3:8][S:9][CH2:10][CH2:11][CH:12]([OH:13])[CH2:2][CH2:3][CH2:4][S:5][CH3:6]1-Chloro-3-methylthiopropane (3.73 g, 30 mmole) in dry THF (50 mL) was added to stirred magnesium turnings (0.72 g, 30 mmole) under argon. Once the addition was complete, the mixture was heated to 50° C. for 3 hours. The mixture was then allowed to cool to room temperature and 3-methylthiopropanal (3.12 g, 30 mmole) was added. The reaction was stirred at room temperature for 1 hour. 2M ammonium chloride solution (50 mL) was added, followed by ether (50 mL). The organics were separated, dried, filtered, and evaporated to give a pale yellow oil that was purified by chromatography in 40-60 petroleum ether/ether (4/5) to give 5 (2.1 g, 36%) as a colorless oil.
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