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Triethylamine → 5-(4'-Ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide

HRID 654342
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 654342
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:4][C:3]=1[O:15][CH3:16].C([N:19]([CH2:22][CH3:23])CC)C.[C:24](Cl)(=[O:28])[O:25][CH2:26][CH3:27]>C(Cl)Cl>[CH2:22]([NH:19][C:12](=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][C:24]([O:25][CH2:26][CH3:27])=[O:28])=[C:3]([O:15][CH3:16])[CH:4]=1)/[CH:23]=[C:11](/[CH2:10][CH2:9][CH:8]=[C:5]([CH3:6])[CH3:4])\[CH3:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 542168095-(4-Hydroxy-3-methoxyphenyl)penta-2,4-dienoic acid

Produkt 1

HCID 867459905-(4'-Ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Separately, 2.33 g of 5-(4'-hydroxy-3'-methoxyphenyl)pentadienoic acid is suspended in 50 ml of methylene chloride under an argon atmosphere. To the suspension cooled to -10° C. are added 2.95 ml of triethylamine and 2.03 ml of ethyl chlorocarbonate. To the mixture, after stirred for 30 min., is added a suspension of the geranylamine-hydrazide mixture in methylene chloride. The resulting mixture is stirred at -10° C. to 0° C. for 4 hours. The reaction mixture is filtered, and precipitates are washed with methylene chloride. Combined filtrate and washing are washed successively with water and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure, and the residue is subjected to column chromatography on silica gel. From the fraction eluted with chloroform is obtained 2.61 g of 5-(4'-ethoxycarbonyloxy-3'methoxyphenyl)pentadienoic acid geranylamide.

Aufarbeitung

  1. additionis added
  2. stirringThe resulting mixture is stirred at -10° C. to 0° C. for 4 hours
  3. filtrationThe reaction mixture is filtered
  4. customprecipitates
  5. washare washed with methylene chloride
  6. washCombined filtrate and washing
  7. washare washed successively with water and saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is distilled off under reduced pressure
  10. washFrom the fraction eluted with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-210e7e0b83344971938b661da57056c9
Quelldatensatz
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05130483

Notizen zur Reaktion

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