[CH2:1]([C:4]1[C:13]([NH:14][C:15](=[O:17])[CH3:16])=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:18])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH3:26][O:27][CH2:28]Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:26][O:27][CH2:28][O:18][C:5]1[C:4]([CH2:1][CH:2]=[CH2:3])=[C:13]([NH:14][C:15](=[O:17])[CH3:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]To a solution of 10 g (40.2 mmol) of methyl 3-allyl-4-acetylaminosalicylate in 50 ml of CH2Cl2 is added 7.9 ml (56.3 mmol) of triethylamine in one portion at room temperature, followed by 3.3 ml (44.2 mmol) of chloromethyl methyl ether dropwise at room temperature. Stirring is continued for 24 hours at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated. Flash chromatography (10% EtOAc/hexanes) affords pure methyl 2-methoxymethyloxy-3-allyl-4-acetylaminobenzoate.
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