[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([OH:11])[C:4]=2[CH:3]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.CCOCC>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([O:11][CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19][O:14]3)[C:4]=2[CH:3]=1A mixture of 1.88 g (7.8 mmol) of (±)-3-bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol, 1.07 mL (11.7 mmol, 1.5 equiv) of 3,4-dihydro-2H-pyran, and 0.20 g (0.80 mmol, 0.1 equiv) of pyridinium p-toluenesulfonate in 38 mL of methylene chloride was stirred under nitrogen at ambient temperature overnight. The mixture was diluted with 115 mL of ether, washed with 45 mL of half-saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated to give 2.8 g of a cloudy oil. Purification by flash chromatography (5-30% ethyl acetate in hexanes) gave the product as a colorless oil. MS (m+1)=327.0; 1H NMR (400 MHz, CDCl3) 7.68 (s, 0.5H), 7.39 (d, 0.5H, J 2 Hz), 7.25 (m, 1H), 6.95 (m, 1H), 4.90 (t, 0.5H, J 3 Hz), 4.80 (m, 1H), 4.48 (t, 0.5H, J 3 Hz), 3.95 (m, 0.5H), 3.67 (m, 0.5H), 3.52 (m, 0.5H), 3.42 (m, 0.5H), 2.85 (m, 1H), 2.67 (m, 1H), 2.10-1.83 (m, 3.5H), 1.82-1.52 (m, 8H), 1.43 (m, 0.5H).
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