[OH:1][CH:2]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23](Br)([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.[Ag-]=O>[C:23]([O:1][CH:2]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:26])([CH3:25])[CH3:24]A mixture of ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate (2c) (190 mg, 0.6 mmol), silver (I) oxide (417 mg, 1.8 mmol) and tertbutylbromide (360 μL, 3.2 mmol) in cyclohexane (5 mL) was vigorously stirred for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (2d) as a white solid (30 mg, 0.08 mmol, 13%).
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