4-Methoxy-3-nitrobenzaldehyde → (3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanol

HRID 971036Notes

Reaction equation

HRID 971036 reaction equation
NC1C=C(C(C2C=CC(OC)=C(OC)C=2)=CC#N)C=CC=1OC.[CH2:24]([O:26][C:27]1[CH:28]=[C:29](Br)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH3:25].[Mg].[CH3:37][O:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][C:40]=1[N+:47]([O-:49])=[O:48]>>[CH3:37][O:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]([C:29]2[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([O:26][CH2:24][CH3:25])[CH:28]=2)[OH:44])=[CH:41][C:40]=1[N+:47]([O-:49])=[O:48]

Participants

5

Reactant 4

HCID 7006084-Methoxy-3-nitrobenzaldehydeHCID 5462224MagnesiumHCID 217726904-Bromo-2-ethoxy-1-methoxybenzeneHCID 689400613-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile

Product 1

HCID 69203000(3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanolYield 42.4%

Procedure

(4-Methoxy-3-nitro-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol was prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile using 3-ethoxy-4-methoxy-bromobenzene (7.6 g, 33 mmol), magnesium turning (0.8 g, 33 mmol) and 4-methoxy-3-nitro-benzaldehyde (5.0 g, 27.6 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford (4-methoxy-3-nitro-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol (3.9 g, 42%): 1H NMR (CDCl3) δ 7.88 (d, J=2 Hz, 1H), 7.53-7.49 (dd, J=3, 9 Hz, 1H), 7.05 (d, J=8 Hz, 1H), 6.84 (s, 3H), 5.75 (d, J=3 Hz, 1H), 4.01 (m, 2H), 3.94 (s, 3H), 3.86 (s, 3H), 2.30 (d, J=3 Hz, 1H), 1.44 (t, 3H).

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1)

Sources & evidence

ORD record
ord-f3a46903e548460a9e08abd30ecc1390
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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