StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triphenylphosphine → 1-(4-[(E)-hex-2-enyloxy]phenyl)-4-pentylbicyclo[2.2.2]octane

HRID 635133
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 635133
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([OH:26])/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25].[CH2:27]([C:32]12[CH2:39][CH2:38][C:35]([C:40]3[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=3)([CH2:36][CH2:37]1)[CH2:34][CH2:33]2)[CH2:28][CH2:29][CH2:30][CH3:31].CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:20]([O:26][C:43]1[CH:44]=[CH:45][C:40]([C:35]23[CH2:38][CH2:39][C:32]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])([CH2:37][CH2:36]2)[CH2:33][CH2:34]3)=[CH:41][CH:42]=1)/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 53180422-Hexen-1-olHCID 5462977Diethyl azodicarboxylateHCID 21257800Phenol, 4-(4-pentylbicyclo[2.2.2]oct-1-yl)-

Produkt 1

HCID 212577911-(4-[(E)-hex-2-enyloxy]phenyl)-4-pentylbicyclo[2.2.2]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

Triphenylphosphine (0.34 g, 0.0013 mol) was added in small portions to a solution of (E)-hex-2-en-1-ol (0.13 g, 0.0013 mol), 4-(4-pentylbicyclo[2.2.2]octyl)phenol (0.35 g, 0.0013 mol), diethylazodicarboxylate (0.22 g, 0.0013 mol) in dry tetrahydrofuran (20 cm3), cooled in an ice bath under an atmosphere of nitrogen. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C./ethyl acetate mixture as eluent, followed by recrystallisation from ethanol to yield 0.18 g (39%), K 69° C., SA-N 59° C., N-I 134° C.

Aufarbeitung

  1. temperaturecooled in an ice bath under an atmosphere of nitrogen
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C./ethyl acetate mixture as eluent
  4. customfollowed by recrystallisation from ethanol
  5. customto yield 0.18 g (39%), K 69° C., SA-N 59° C., N-I 134° C.

Quellen und Nachweise

ORD-Eintrag
ord-20aad75121be4c4ab75a9846bc46596a
Quelldatensatz
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06187393B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion