3,5-Dimethoxybenzaldehyde → HCID 69204689, compound

HRID 2378241Notes

Reaction equation

HRID 2378241 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[C:4]([O:16][CH3:17])[CH:3]=1.C([Li])CCC.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([O:33][CH3:34])[CH:32]=1)[CH:28]=[O:29].COC1C=C(C(C2C=CC=C(OC)C=2)=CC#N)C=C(OC)C=1>>[C:10]([Si:7]([CH3:9])([CH3:8])[O:6][C:5]1[CH:14]=[CH:15][C:2]([CH:28]([C:27]2[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:25]([O:24][CH3:23])[CH:26]=2)[OH:29])=[CH:3][C:4]=1[O:16][CH3:17])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 4

HCID 817473,5-DimethoxybenzaldehydeHCID 11209312HCID 11209312, compoundHCID 692052993-(3,5-Dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrileHCID 178418339Butyllithium

Product 1

HCID 69204689HCID 69204689, compound

Procedure

(4-bromo-2-methoxyphenoxy)-tert-butyldimethylsilane (4.37 g, 13.77 mmol), n-butyl lithium (5.51 ml, 13.77 mmol), and 3,5-dimethoxybenzaldehyde (2.08 g, 12.52 mmol) were treated in the same manner as described above for the synthesis of 3-(3,5-dimethoxy-phenyl)-3-(3-methoxy-phenyl)-acrylonitrile. The crude was purified via flash column chromatography (5% EtOAc in hexane gradient to 20% EtOAc in hexane in about 40 min.) to give [4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanol a clear oil (3.94 g, 78%): 1HNMR (CDCl3) 6.89 (s, wide, 1H, Ar), 6.78 (s, wide, 2H, Ar), 6.53 (d, J=2 Hz, 2H, Ar), 6.36 (t, J=2 Hz, 1H, Ar), 5.69 (d, J=3 Hz, 1H, CHOH), 3.77 (s, 3H, OCH3), 3.76 (s, 6H, 2OCH3), 2.19 (d, J=3 Hz, 1H, OH), 0.98 (s, 9H, 3CH3), 0.14 (s, 6H, 2CH3). The product was carried over to the next step.

Workup

  1. customThe crude was purified via flash column chromatography (5% EtOAc in hexane gradient to 20% EtOAc in hexane in about 40 min.)

Sources & evidence

ORD record
ord-b73b3132cbd14b71b34fad352d33e094
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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