Br[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:9][S:10](=[S:13])([O-:12])=[O:11].[Na+].CN(C=O)C>O>[CH3:9][S:10](=[S:13])([O:12][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=[O:11]The reaction mixture of bromomethylcyclohexane (1.560 g, 0.00881 mol), sodium methanethiosulfonate (1.180 g, 0.00881 mol) and dry DMF (6 mL) was heated at 50° C. for 24 hr. At room temperature, water (15 mL) was added and the mixture was extracted with ether (3×30 mL). The extracts were washed with brine, dried, concentrated and the residue was subjected to flash column chromatography on silica gel with EtOAc-hexanes (1:4) to afford a colorless oil (1.5033 g, 82%). IR (CDCl3 cast): 3030 (w), 3012 (w), 2926 (st), 2853 (st), 1446 (m), 1410 (m), 1320 (st), 1134 (st), 955 (st), 746 cm−1 (st); 1H NMR (200 MHz, CDCl3): δ 3.32 (s, 3H, CH3SO2S), 3.07 (d, J=6.9 Hz, 2H, SCH2CH), 1.95-1.55 (m, 6H), 1.40-0.90 (m, 5H); 13C NMR (50 MHz, CDCl3): δ 50.42, 43.30, 37.83, 32.43, 26.02, 25.82.
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