2-Chlorophenol → HCID 87327125, Verbindung

HRID 1845870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845870
[Br:1][C:2]1[N:7]=[C:6]([C@@H:8]([OH:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C@H:8]([O:10][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])[CH3:9])[N:7]=1

Komponenten

6

Edukt 4

HCID 72452-ChlorophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10910574HCID 10910574, Verbindung

Produkt 1

HCID 87327125HCID 87327125, VerbindungAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of (S)-1-(6-bromopyridin-2-yl)ethanol (1 g) (prepared by the method of S. Ishikawa, T. Hamada, K. Manabe, and S. Kobayashi, Synthesis 2005, 13, 2176-2182), 2-chlorophenol (0.615 mL, 0.764 g) and triphenylphosphine (1.558 g) in tetrahydrofuran (20 mL) under N2 and cooled to 0° C. A solution of diisopropyl azodicarboxylate (1.17 mL, 1.2 g) in tetrahydrofuran (10 mL) was then added dropwise and reaction warmed to room temperature overnight. The solvent was removed under reduced pressure, then heptane added to precipitate the triphenylphosphine oxide side product. Filtration and evaporation of the filtrate followed by purification by flash chromatography on silica eluting with heptane/ethyl acetate 8:2 gave the title compound (1.45 g) as a clear liquid.

Aufarbeitung

  1. customreaction
  2. temperaturewarmed to room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. additionheptane added
  5. customto precipitate the triphenylphosphine oxide side product
  6. filtrationFiltration and evaporation of the filtrate
  7. customfollowed by purification by flash chromatography on silica eluting with heptane/ethyl acetate 8:2

Quellen und Nachweise

ORD-Eintrag
ord-052ef5ac67eb46fe9f24aee456903675
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952001B2

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