Triphenylphosphine → 3-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol

HRID 325051

Reaktionsgleichung

Reaktionsgleichung von HRID 325051
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[C:35]([OH:40])[CH:34]=1.[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50]O)=[CH:45][CH:44]=1)#[N:42]>C(Cl)Cl.CCOCC>[Cl:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[C:35]([O:40][CH2:50][CH2:49][C:46]2[CH:47]=[CH:48][C:43]([C:41]#[N:42])=[CH:44][CH:45]=2)[CH:34]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 945541,3-Benzenediol, 5-chloro-HCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 220335343-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenolAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triphenylphoshine (32 g; 122 mmol) and diethylazodicarboxylate (19.2 mL; 122 mmol) were dissolved in CH2Cl2 (150 mL). Chloro-3,5-dihydroxybenzene (9.1 g; 63 mmol; from step (i) above) and 2-(4-cyanophenyl)ethanol (9.04 g; 61 mmol) were added and the solution was stirred at room temperature overnight. The mixture was diluted with Et2O and filtered through Celite. The solvent was removed in vacuo. Purification, first by flash chromatography (SiO2; CH2Cl2:MeOH), then by preparative HPLC (60% CH3CN:0.1 M NH4OAc/aq), afforded 3.55 g (21%) of the sub-title compound.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customThe solvent was removed in vacuo
  3. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-b142d67c5d7743cc8446130949fd67d9
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06221898B1

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