[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=[CH:2]1.[C:16](Br)([CH3:19])([CH3:18])[CH3:17]>C1CCCCC1.ClCCl.[Ag-]=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH:10]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:2]1A mixture of methyl 2-(1-benzothiophen-3-yl)-2-hydroxyacetate (4a) (300 mg, 1.35 mmol), silver (I) oxide (938 mg, 4.05 mmol) and tertbutylbromide (910 μL, 8.1 mmol) in a mixture of cyclohexane (5 mL) and dichloromethane (1 mL) was vigorously stirred for 20 hours under a nitrogen atmosphere. 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 (4b) as a white solid (70 mg, 0.25 mmol, 10%).
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