Diethyl Ether → HCID 69205023, compound

HRID 971035Notes

Reaction equation

HRID 971035 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:35]2[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[C:37]([O:43][CH3:44])[CH:36]=2)=[CH:32][C:33]#[N:34])=[CH:27][C:26]=1[O:45][CH3:46])(C)(C)C.CCOCC>C1COCC1>[CH3:42][O:41][C:39]1[CH:40]=[C:35]([C:31]([C:28]2[CH:29]=[CH:30][C:25]([OH:24])=[C:26]([O:45][CH3:46])[CH:27]=2)=[CH:32][C:33]#[N:34])[CH:36]=[C:37]([O:43][CH3:44])[CH:38]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 69205834HCID 69205834, compound

Product 1

HCID 69205023HCID 69205023, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M solution in THF, 5.55 ml, 5.55 mmol) was added at rt to a stirred solution of 3-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-3-(3,5-dimethoxy-phenyl)-acrylonitrile (1.97 g, 4.63 mmol) in THF (35 ml). The colorless clear solution immediately turned into brown/red wine color. The reaction should be done within one hour. Ice water (15 ml) was poured into the reddish solution, followed by addition of ether (80 ml). The mixture was washed with water (2×100 ml), dried over MgSO4, filtered and concentrated to a yellow oil, which was lyophilized to give 3-(3,5-dimethoxy-phenyl)-3-(4-hydroxy-3-methoxy-phenyl)-acrylonitrile as a white gummy solid (1.26 g, 88%): mp, 120-122° C.; 1HNMR (DMSO-d6) δ 9.68 (s, 1H, OH group of one isomer), 9.60 (s, 1H, OH group of the other isomer), 7.11-6.61 (m, 8H, Ar), 6.49-6.46 (m, 4H, Ar), 6.23 (s, 1H, double bond proton of one isomer), 6.11 (s, 1H, double bond proton of the other isomer), 3.78-3.74 (multiple singlets, 18H, 6OCH3), isomer ratio based on 1HNMR was 49%:51%; 13C NMR (CDCl3) δ 163.0, 162.9, 160.9, 160.8, 148.2, 147.7, 146.6, 146.3, 141.6, 139.2, 130.9, 128.9, 124.2, 122.9, 118.5, 118.2, 114.6, 114.5, 112.3, 110.6, 107.9, 107.2, 102.3, 102.2, 93.7, 93.1, 56.4, 56.2, 55.7, 55.6; Anal. Calcd. For C18H17NO4: C, 69.44; H, 5.50; N, 4.50. Found: C, 69.24; H, 5.38; N, 4.27.

Workup

  1. customThe reaction
  2. washThe mixture was washed with water (2×100 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil, which

Sources & evidence

ORD record
ord-78ff6ee5146248cca19cabc2e07ff31d
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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