Triphenylphosphine → N-[2-(2-cyclohexen-1-yloxy)phenyl]acetamide

HRID 496189

Reaktionsgleichung

Reaktionsgleichung von HRID 496189
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O)(=[O:10])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(=O)ON=NOC(=O)OCC)C>C1COCC1>[CH:1]1([O:7][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:8](=[O:10])[CH3:9])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 119722-AcetamidophenolHCID 131982-Cyclohexen-1-OLHCID 54051361Diethyl azodicarbonic acid

Produkt 1

HCID 22313659N-[2-(2-cyclohexen-1-yloxy)phenyl]acetamideAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-Cyclohexenol (491 mg, 0.49 ml, 5.00 mmol, 1.0 equiv.), 2-acetamidophenol (756 mg, 5.00 mmol, 1.0 equiv.) and triphenylphosphine (1.44 g, 5.50 mmol, 1.1 equiv.) were dissolved in THF (10 ml) and kept at ambient temperature by a water bath. After dropwise addition of diethyl azodicarbonic acid (871 mg, 0.78 ml, 5.00 mmol, 1.0 equiv.), dissolved in THF (3 ml), the reaction mixture was stirred over night. Extractive work-up and flash chromatography on silica gel (heptane/tertbutyl(methyl)ether=1:1) afforded 224 mg (19%) the title compound as a yellow oil.

Aufarbeitung

  1. customkept at ambient temperature by a water bath

Quellen und Nachweise

ORD-Eintrag
ord-bfa86f5257fc4cc08e7b8fb76e4ff145
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943188B2

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