[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19]Br)[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:15]([O:17][CH:18]([O:21][CH2:22][CH3:23])[CH2:19][O:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[CH3:16]A mixture of 4-(phenylthio)phenol (4.7 g, 23 mmol), bromoacetaldehyde diethyl acetal (4.3 mL, 28 mmol) and K2CO3 (3.82 g, 28 mmol) in DMF (40 mL) was stirred at reflux for 6 h. The reaction mixture was allowed to cool down to room temperature and poured over ice and diluted to 100 mL with water. The solution was extracted with Et2O (20 mL×3); the combined extracts were washed with 1N NaOH solution, water and brine, dried, and concentrated under reduced pressure to yield a yellow oil that was used without further purification: 1H NMR (400 MHz, CDCl3) δ 7.42 (d, 2H), 7.27-7.06 (m, 5H), 6.92 (d, 2H), 4.84 (t, 1H), 4.02 (d, 2H), 3.84-3.68 (m, 4H), 1.13 (m, 6H).
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