[CH3:1][O:2][C:3]1(C2C=C(CBr)C=CC=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C(OC)(=O)C[SH:19].[CH2:23]1[CH2:33][CH2:32]N2[C:26](=NCCC2)[CH2:25][CH2:24]1.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1([C:33]2[CH:32]=[C:26]([CH:35]([CH3:34])[C:36]([O:37][CH3:38])=[S:19])[CH:25]=[CH:24][CH:23]=2)[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1
A solution of 3-[(4-methoxy)tetrahydropyran-4-yl]-α-bromotoluene (1.0 g, 3.87 mmol) in 10 mL of anhydrous THF was cooled to 5° C. A solution of methyl thioglycolate (0.41 g, 3.87 mmol) and DBU (0.59 g, 3.87 mmol) in 10 mL of THF was added while maintaining the temperature at 5° C. The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with 250 mL of ethyl acetate, and the organic layer was washed with 1 N HCl (2×100 mL), saturated sodium bicarbonate (1×100 mL), brine (1×100 mL), dried over magnesium sulfate, filtered and concentrated. The concentrated residue was purified by flash column chromatography on silica gel, eluting with 40% ethyl acetate in hexane, to give 0.87 g (72%) of methyl 3-[(4-methoxy)-tetrahydropyran-4-yl]phenyl-methylthioacetate as a clear oil: 1H NMR (CDCl3/300 MHz) δ 1.94-2.09 (m, 4H), 2.97 (s, 3H), 3.08 (s, 2H), 3.73 (s, 3H), 3.77-3.92 (m, 6H), 7.26-7.36 (m, 4H). HRMS calcd for C16H22O4S 311.1317. Found 311.1271.
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