Tributylphosphine → HCID 59364057, Verbindung

HRID 1691539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691539
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[O:15]([C:22]1[CH:23]=[C:24]([CH2:28]O)[CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[O:15]([C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 13831TributylphosphineHCID 262953-Phenoxybenzyl alcoholHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59364069Methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate

Produkt 1

HCID 59364057HCID 59364057, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.158 g, 0.822 mmol), (3-phenoxyphenyl)methanol (0.150 g, 0.747 mmol) and tributylphosphine (0.301 g, 1.49 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.375 g, 1.49 mmol) was added, and the mixture was stirred at room temperature for 60 hr. Hexane (15 mL) was added to the reaction mixture, and the precipitated insoluble material was filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.221 g, yield 72%) as colorless crystals.

Aufarbeitung

  1. filtrationthe precipitated insoluble material was filtrated
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70)

Quellen und Nachweise

ORD-Eintrag
ord-4f1502a6d2eb4a92aaf120c8e6962a75
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153694B2

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