Triphenylphosphine → 1-Benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene

HRID 618407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618407
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][OH:13])=[O:8])=[CH:5][CH:4]=1.[CH2:18]([O:25][C:26]1[CH:31]=[C:30]([Cl:32])[C:29](O)=[C:28]([Cl:34])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.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>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([Cl:34])[C:29]([O:13][CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[C:6]2[CH:14]=[CH:15][C:3]([C:2]([F:16])([F:17])[F:1])=[CH:4][CH:5]=2)=[C:30]([Cl:32])[CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 120841702,6-Dichloro-4-benzyloxyphenolHCID 220068303-(4-Trifluoromethylbenzamido)propan-1-ol

Produkt 1

HCID 220068441-Benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A reaction vessel was charged with 5.25 g (21.2 mmol) of 3-(4-(trifluoromethyl)benzamido)propan-1-ol, 5.72 g (21.2 mmol) of 4-benzyloxy-2,6-dichlorophenol, 5.29 g (20.2 mmol) of triphenylphosphine and 100 ml of tetrahydrofuran, and a solution of 4.08 g (20.2 mmol) of diisopropyl azodicarboxylate dissolved in 20 ml of tetrahydrofuran was added dropwise, while stirring. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and the residue was subjected to silica gel chromatography, which afforded 1-benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene. 1-Benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene was dissolved in ethyl acetate, which was put into a reaction vessel, and the air in the vessel was replaced with nitrogen gas. A catalytic amount of 10% palladium on carbon was added, and the nitrogen gas in the vessel was replaced with hydrogen gas, followed by vigorous stirring at room temperature for 24 hours. The hydrogen gas in the vessel was replaced with nitrogen gas, after which the reaction mixture was filtered through cerite and the filtrate was concentrated to give 3,5-dichloro-4-(33-(4-trifluoromethylbenzamido)propyloxy)phenol.

Aufarbeitung

  1. additionwas added dropwise
  2. stirringAfter stirring at room temperature for 12 hours
  3. concentrationthe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-efc13577df7448fd9d7745d77bad0c54
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952386

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