Magnesium → (3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol

Reaction equation

NC1C=C(C([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)=CC#N)C=CC=1OC.[Mg].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36])[CH:30]=[O:31]>>[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:30]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[OH:31])[CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36]

Participants

Reactant 3

HCID 5462224Magnesium

HCID 114920433-Methoxy-4-nitrobenzaldehyde

HCID 689400613-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile

Product 1

HCID 69205180(3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanolYield 72%

Procedure

(3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol was prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile using 3,4-bromoveratrole (2.5 g, 11.5 mmol), magnesium turning (0.3 g, 11.5 mmol) and 3-methoxy-4-nitro-benzaldehyde (1.5 g, 8.2 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford (3-methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol (1.9 g, 72%): 1H NMR (CDCl3) δ 7.80 (d, J=8 Hz, 1H), 7.22 (s, 1H), 6.98-6.85 (m, 4H), 5.79 (d, J=2 Hz, 1H), 3.97 (s, 3H), 3.87 (s, 6H).