[Mg].[CH2:2](Br)[CH3:3].[CH2:5]([Mg]Br)[CH3:6].[NH:9]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][O:16][C:17]2=[O:18])[C:10]([CH3:12])=[O:11].[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH2:5]([C:17]([OH:18])([CH2:2][CH3:3])[C:19]1[CH:20]=[CH:21][CH:22]=[C:13]([NH:9][C:10]([CH3:12])=[O:11])[C:14]=1[CH2:15][OH:16])[CH3:6]
To a mixture of 9.5 g of metallic magnesium and 60 ml of diethyl ether was slowly added with stirring a solution of 43 g of ethyl bromide in 120 ml of diethyl ether. The mixed solution was heated for 15 minutes under refluxing and left to stand for cooling. The solution of ethylmagnesium bromide thus prepared above in ether was slowly added with stirring at inner temperature of below 10° C. to a solution of 7.5 g of 4-acetaminophthalide in 120 ml of tetrahydrofuran, followed by stirring at room temperature overnight. After the reaction was over, the reaction mixture was poured into aqueous ammonium chloride solution (saturated) under ice cooling and extracted twice with 400 ml of ethyl acetate. The combined extracts were concentrated to obtain an oily substance. The oily substance was purified by silica gel column chromatography to obtain 8.0 g of α,α-diethyl-2-hydroxymethyl-3-acetaminobenzyl alcohol in the colorness oily substance.
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