Triphenylphosphine → 6-[(3-Ethynylphenyloxy)methyl]-1,2-dithiin

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To a stirred solution of 3-(hydroxymethyl)-6-[(tert-butyldimethylsilyloxy)methyl]-1,2-dithiin (U.S. Ser. No. 08/212,096) (235 mg, 0.802 mmol) in 1 mL of dry THF was added a solution of 3-hydroxyphenylacetylene (142 mg, 1.20 mmol) in 1 mL THF, followed by the addition of triphenylphosphine (315 mg, 0.977 mmol). The resulting solution was cooled to 0° C., then 190 μL (210 mg, 1.037 mmol) of diethylazodicarboxylate was added, and the reaction mixture was kept at 0°-5° C. for 1.5 h until TLC analysis showed the reaction to be complete. For 5 isolation of the products, the reaction mixture was chromatographed directly on a silica gel column, using ethyl acetate-hexane, 1:20, to yield 3-[tert-butyldimethylsilyloxy)methyl]-6-[(3-ethynylphenyloxy)methyl]-1,2-dithiin (175 mg, 56.0%); 1H-NMR (CDCl3) δ7.23 (t, J=8.0, 1 H), 7.12 (d, J=8.0, 1 H), 7.05 (s, 1 H), 6.93 (dd, J=6.0, 2.4, 1 H), 6.44 (d, J=6.0, 1 H), 6.37 (d, J=6.0, 1 H), 4.66 (s, 2 H), 4.30 (s, 2 H), 3.07 (bs, 1 H), 0.92 (s, 9 H), 0.10 (s, 6 H); 13C--NMR (CDCl3) δ157.79, 136.21, 132.54, 129.46, 128.74, 127.03, 125.43, 123.45, 118.29, 116.22, 83.28, 77.21, 69.73, 64.79, 25.76, 18.31, -5.41. MS (EI) 390.1 (M+).

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