Potassium Carbonate → Methyl 4-((3E)-2-[2-(4-cyanophenyl)ethyl]-4-{2-[(5-phenylpentyl)oxy]phenyl}but-3-en-1-yl)benzoate

HRID 1913762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1913762
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.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: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[O:49][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:30][C:31]2[CH:32]=[CH:33][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:39][CH:40]=2)=[CH:23][CH:22]=1)#[N:20]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 285561(5-Bromopentyl)benzeneHCID 57831366Methyl E-4-[2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-enyl]benzoate

Produkt 1

HCID 57831394Methyl 4-((3E)-2-[2-(4-cyanophenyl)ethyl]-4-{2-[(5-phenylpentyl)oxy]phenyl}but-3-en-1-yl)benzoateAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

464.2 mg (2.04 mmol) of (5-bromopentyl)benzene and 353.05 mg (2.55 mmol) of potassium carbonate are added to a solution of 700.8 mg (1.7 mmol) of methyl 4-[(3E)-2-[2-(4-cyanophenyl)ethyl]-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 65 ml of acetonitrile, and the mixture is stirred under reflux for 12 hours. After cooling, the potassium carbonate is filtered off and the filtrate is evaporated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 945 mg (1.7 mmol, 99.5% yield) are obtained.

Aufarbeitung

  1. temperatureunder reflux for 12 hours
  2. temperatureAfter cooling
  3. filtrationthe potassium carbonate is filtered off
  4. customthe filtrate is evaporated
  5. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)
  6. custom945 mg (1.7 mmol, 99.5% yield) are obtained

Quellen und Nachweise

ORD-Eintrag
ord-1dbe816e81a548d48961f1ac6b3cf7fb
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609727B2

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