4-Benzylphenol → 2-(4-Benzyloxyphenyl)-1-[3-(4-benzylphenoxy)propyl]-5-methyl-1H-pyrrole

HRID 1072747

Reaktionsgleichung

Reaktionsgleichung von HRID 1072747
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:21][CH2:22][CH2:23][OH:24])[C:17]([CH3:20])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:21][CH2:22][CH2:23][O:24][C:35]3[CH:36]=[CH:37][C:32]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:33][CH:34]=3)[C:17]([CH3:20])=[CH:18][CH:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 75634-BenzylphenolHCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 223873173-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-ol

Produkt 1

HCID 223875892-(4-Benzyloxyphenyl)-1-[3-(4-benzylphenoxy)propyl]-5-methyl-1H-pyrroleAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-[2-(4-benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-ol (1.00 g, 3.11 mmol), 4-benzylphenol (572 mg, 3.11 mmol) and triphenylphosphine (1.22 g, 4.67 mmol) in toluene (2 ml) was added 1,1′-(azodicarbonyl)dipiperidine (1.18 g, 4.67 mmol) and the mixture was stirred at 80° C. for 12 hours. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate anhydride and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the object compound as an oily substance. 1.21 g (yield: 79.6%)

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate anhydride
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)
  5. customto give the object compound as an oily substance

Quellen und Nachweise

ORD-Eintrag
ord-5a525e1ae344464b819331b1ab52c859
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911468B2

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