5-[(2-Methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carbaldehyde → Cyclohexyl{5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-yl}methanol
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:18])[C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH:14]=[O:15])=[C:11]([CH3:16])[C:10]=2[CH:17]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCCC1>[CH:19]1([CH:14]([C:12]2[O:13][C:9]3[CH:8]=[CH:7][C:6]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:18])=[CH:17][C:10]=3[C:11]=2[CH3:16])[OH:15])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1Participants
4
Procedure
To a solution (5 mL) of 5-[(2-methoxyethyl)(methyl)amino]-3-methyl-1-benzofuran-2-carbaldehyde (0.09 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise cyclohexylmagnesium bromide (2 mL, 1M tetrahydrofuran solution) under ice-cooling. After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.11 g, quantitative) as a yellow oil.