Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:12][S:13](=[S:16])([O-:15])=[O:14].[Na+].CN(C=O)C>O>[CH3:12][S:13](=[S:16])([O:15][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:14]The mixture of 1-bromodecane (2.095 g, 0.00947 mol), sodium methanethiosulfonate and dry DMF (6 mL) was heated at 60° C. for 2 hr. At room temperature, water (15 mL) was added and the mixture was extracted with ether (3×30 mL). The ether 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 white solid (2.063 g, 94%). It was recrystallized from 95% EtOH. mp: 28.0-29.5° C. IR (CDCl3 cast): 2954 (m), 2921 (st), 2852 (st), 1469 (m), 1305 (st), 1128 (st), 965 (m), 758 (m) and 720 cm−1 (m); 1H NMR (200 MHz, CDCl3): δ 3.32 (s, 3H, CH3SO2S), 3.17 (t, J=7.4 Hz, 2H, SCH2CH2), 1.77 (m, 2H, SCH2CH2), 1.50-1.20 (m, 14H, —(CH2)7—), 0.88 (m, 3H, CH2CH3); 13C NMR (50 MHz, CDCl3): δ 50.64, 36.49, 31.84, 29.45 (two carbons), 29.37, 29.23, 28.94, 28.57, 22.64, 14.08.
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