Triphenylphosphine → 3-(4-(Trifluoromethyl)benzamido)propyloxyphenyl benzoate

HRID 377732

Reaktionsgleichung

Reaktionsgleichung von HRID 377732
[C:1]([O:9][C:10]1[CH:15]=[C:14](C)[C:13](O)=[C:12](CC)[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:34]=[CH:33][C:25]([C:26]([NH:28][CH2:29][CH2:30][CH2:31][OH:32])=[O:27])=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[C:1]([O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[O:32][CH2:31][CH2:30][CH2:29][NH:28][C:26](=[O:27])[C:25]1[CH:33]=[CH:34][C:22]([C:21]([F:35])([F:36])[F:20])=[CH:23][CH:24]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 220068303-(4-Trifluoromethylbenzamido)propan-1-olHCID 232824092-Ethyl-6-methyl-4-benzoyloxyphenol

Produkt 1

HCID 867544953-(4-(Trifluoromethyl)benzamido)propyloxyphenyl benzoateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of 0.5 g of crude 3-ethyl-4-hydroxy-5-methylphenyl benzoate, 0.48 g of 3-(4-(trifluoromethyl)benzamido)propan-1-ol, 0.54 g of triphenylphosphine and 10 ml of tetrahydrofuran was added dropwise a solution of 0.41 g of diisopropylazodicarboxylate dissolved in 2 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated under reduced pressure to give a residue. The residue was subjected to silica gel chromatography, which afforded 0.87 g of 3-ethyl-5-methyl-4-(3-(4-(trifluromethyl)benzamido)propyloxyphenyl benzoate (90% yield).

Aufarbeitung

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-e0d9a0333a1c4cfda6efcf4fd2422423
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028100

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