[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].I[CH3:19]>C(Cl)(Cl)Cl.[Ag]=O>[CH3:19][O:17][CH2:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1To a solution of 0.19 g (0.81 mmole) of ethyl 4-(hydroxymethyl)-3-methyl-1-benzofuran-2-carboxylate (Example 92, Step 2) in 2 mL of chloroform was added silver (II) oxide (0.34 g, 1.46 mmol, 1.8 eq) and 2 mL of iodomethane and the mixture was heated in sealed tube at ˜55° C. for 4.5 days. The reaction was filtered and concentrated in vacuo to provide 0.20 g of ethyl 4-(methoxymethyl)-3-methyl-1-benzofuran-2-carboxylate. Yield: ˜93.8% m.p. 45-47° C.; MS: 249.1(M+H)+.
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