Triphenylphosphine → 3-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

HRID 497045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497045
[C:1]([C:4]1[C:5]([OH:17])=[C:6]([Cl:16])[CH:7]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([Cl:15])[Cl:14])[CH:9]=1)(=[O:3])[CH3:2].[F:18][C:19]([F:32])([F:31])[C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][CH2:29]O)=[N:24][CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([C:4]1[C:5]([O:17][CH2:29][CH2:28][CH2:27][O:26][C:23]2[CH:22]=[CH:21][C:20]([C:19]([F:32])([F:18])[F:31])=[CH:25][N:24]=2)=[C:6]([Cl:16])[CH:7]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([Cl:15])[Cl:14])[CH:9]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112067993-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-olHCID 114152013-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzene

Produkt 1

HCID 102177823-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under an atmosphere of protective gas, 1.2 g of 3-acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzene, 0.9 g of 3-(5-trifluoromethylpyrid-2-yloxy)propan-1-ol and 1.12 g of triphenylphosphine were dissolved in 35 ml of dry tetrahydrofuran (THF). With ice-bath cooling, 0.74 g of diethyl azodicarboxylate was added dropwise. After about 30 minutes, the ice-bath was removed, and the mixture was stirred at room temperature for 15 hours. The mixture was then concentrated under reduced pressure and the residue was taken up in a mixture of ethyl acetate and water. After shaking, the organic phase was isolated, dried and concentrated under reduced pressure. The crude product was purified chromatographically. Yield: 1.52 g (74%)

Aufarbeitung

  1. temperatureWith ice-bath cooling
  2. customthe ice-bath was removed
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. additionthe residue was taken up in a mixture of ethyl acetate and water
  5. stirringAfter shaking
  6. customthe organic phase was isolated
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified chromatographically

Quellen und Nachweise

ORD-Eintrag
ord-e2df113141a546ef87f6eadd86ed9e64
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949551B2

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