Potassium Carbonate → Methyl 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}-benzoate

HRID 1913761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913761
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH:29](/[CH:41]=[CH:42]/[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[OH:49])[CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[CH:23][CH:22]=1)#[N:20]>C(#N)C>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][O:49][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2/[CH:42]=[CH:41]/[CH:29]([CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=2)[CH2:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57831366Methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate

Produkt 1

HCID 57831375Methyl 4-{(3E)-4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}-benzoateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2.20 g (9.71 mmol) of 4-(tert-butyl)benzyl bromide and 2.02 g (14.59 mmol) of anhydrous potassium carbonate are added to a solution of 2 g (3.6 mmol) of methyl E4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate in 8 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then filtered and the filtrate is evaporated to dryness. The residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 1.9 g (3.30 mmol, 97% purity, 92% yield) of an oil are isolated.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. filtrationThe mixture is then filtered
  4. customthe filtrate is evaporated to dryness
  5. customThe residue is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)
  6. custom1.9 g (3.30 mmol, 97% purity, 92% yield) of an oil are isolated

Quellen und Nachweise

ORD-Eintrag
ord-41e1561e5f394cdfaa36435717fd9263
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609727B2

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