CCN(CC)CC.Cl.[NH2:9][OH:10].[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[CH3:23]>O1CCOCC1.CCOC(C)=O>[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[N:9][OH:10])=[CH:17][C:16]=1[CH3:23]Et3N (1.68 mL, 12.0 mmol) and hydroxylamine hydrochloride (320 mg, 4.64 mmol) were added to a solution of 4-(methoxymethoxy)-3-methylbenzaldehyde (620 mg, 3.44 mmol) in 1,4-dioxane (12 mL). The reaction mixture was sonicated for 10 min and stirred at 25° C. for 3 d. The reaction mixture was diluted with EtOAc and successively washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 3:1) to provide the title compound (580 mg, 86% yield) as a clear gum.
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