Tributylphosphine → HCID 59364070, Verbindung

HRID 1691534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691534
[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]=[S:16]1(=[O:39])[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36]O)[CH:31]=3)=[C:25]([CH3:38])[CH:24]=2)[CH2:18][CH2:17]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[O:15]=[S:16]1(=[O:39])[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][O:1][C:2]4[CH:3]=[CH:4][C:5]([CH:8]5[CH2:10][CH:9]5[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=4)[CH:31]=3)=[C:25]([CH3:38])[CH:24]=2)[CH2:18][CH2:17]1

Komponenten

7

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59342608{4'-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2',6'-dimethylbiphenyl-3-yl}methanolHCID 59364069Methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate

Produkt 1

HCID 59364070HCID 59364070, VerbindungAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.156 g, 0.813 mmol), {4′-[(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)oxy]-2′,6′-dimethylbiphenyl-3-yl}methanol (0.395 g, 0.739 mmol) and tributylphosphine (0.298 g, 1.47 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.372 g, 1.47 mmol) was added, and the mixture was stirred at room temperature for 4 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=20:80-40:60) to give the title compound (0.396 g, yield 91%) as a colorless oil.

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=20:80-40:60)

Quellen und Nachweise

ORD-Eintrag
ord-7a3856da796345259bc51ac9b977fe6b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153694B2

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