Diethyl Ether → 3-(3,5-Dimethoxy-phenyl)-3-(3-hydroxy-4-methoxy-phenyl)-acrylonitrile

HRID 2378167Notes

Reaction equation

HRID 2378167 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:28]=[C:29]([C:35]([C:39]2[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=[C:41]([O:47][CH3:48])[CH:40]=2)=[CH:36][C:37]#[N:38])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34])(C(C)(C)C)(C)C.CCOCC>C1COCC1>[CH3:48][O:47][C:41]1[CH:40]=[C:39]([C:35]([C:29]2[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([OH:26])[CH:28]=2)=[CH:36][C:37]#[N:38])[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 692025173-[3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-3-(3,5-dimethoxyphenyl)acrylonitrile

Product 1

HCID 692025153-(3,5-Dimethoxy-phenyl)-3-(3-hydroxy-4-methoxy-phenyl)-acrylonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M solution in THF, 1.49 ml, 1.49 mmol) was added at rt to a stirred solution of 3-[3-(tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-3-(3,5-dimethoxyphenyl)acrylonitrile (0.53 g, 1.25 mmol) in THF (15 ml). The colorless clear solution immediately turned into brown/red wine color. The reaction should be done within one hour. Ice water (10 ml) was poured into the reddish solution, followed by addition of ether (50 ml). The mixture was washed with water (2×80 ml), dried over MgSO4, filtered and concentrated to a yellow oil, which was lyophilized to give 3-(3,5-dimethoxy-phenyl)-3-(3-hydroxy-4-methoxy-phenyl)-acrylonitrile as a foamy solid (0.35 g, 90%): mp, 43-45° C.; 1HNMR (DMSO-d6) δ 9.36 (s, 1H, OH group of one isomer), 9.28 (s, 1H, OH group of the other isomer), 7.07 (d, J=8 Hz, 1H, Ar), 7.00 (d, J=8 Hz, 1H, Ar), 6.91-6.82 (m, 4H, Ar), 6.69-6.65 (m, 2H, Ar), 6.49 (t, J=2 Hz, 4H, Ar), 6.19 (s, 1H, double bond proton of one isomer), 6.17 (s, 1H, double bond proton of the other isomer), 3.87 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 3.81 (s, 6H, 2OCH3), 3.78 (s, 6H, 2OCH3), isomer ratio based on 1HNMR was 45%: 55%; 13C NMR (CDCl3) δ 162.8, 162.6, 160.8, 160.8, 148.7, 148.2, 145.7, 145.5, 141.4, 139.1, 131.9, 130.2, 122.3, 121.3, 118.2, 118.1, 116.0, 114.4, 110.4, 110.4, 107.8, 107.1, 102.2, 94.2, 93.5, 56.2, 56.1, 55.6; Anal. Calcd. For C18H17NO4: C, 69.12; H, 5.53; N, 4.48. Found: C, 68.76; H, 5.69; N, 4.22.

Workup

  1. customThe reaction
  2. washThe mixture was washed with water (2×80 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil, which

Sources & evidence

ORD record
ord-fa9f42e03515462f95b0484b3cd8b5fd
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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