Triphenylphosphine → Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate

HRID 2422310

Reaktionsgleichung

Reaktionsgleichung von HRID 2422310
[NH:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[CH2:14][O:15][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 12882229(3-(Phenylamino)phenyl)methanolHCID 66777355Diethylazodicarboxylate toluene

Produkt 1

HCID 57541953Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of (3-anilinophenyl)methanol (1.12 g, 5.62 mmol), methyl 3-(4-hydroxyphenyl)propanoate (1.22 g, 6.75 mmol), triphenylphosphine (1.92 g, 7.31 mmol) and tetrahydrofuran (20 mL) was added diethyl azodicarboxylate toluene solution (40%, 3.32 mL) with stirring at 0° C. and the mixture was stirred at room temperature for 14 hrs. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give the title compound (1.01 g, yield 50%) as beige crystals.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 14 hrs
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

Quellen und Nachweise

ORD-Eintrag
ord-91d14e223e39464da398c116911a8c17
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960369B2

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