Triphenylphosphine → 2-(2-{3-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propoxy}phenyl)-1,3-benzoxazole

HRID 1072762

Reaktionsgleichung

Reaktionsgleichung von HRID 1072762
[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.O[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[O:33][C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=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:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[O:33][C:34]4[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=4[N:36]=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 11776TriphenylphosphineHCID 132692-(2-Benzoxazolyl)phenolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 223873173-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propan-1-ol

Produkt 1

HCID 223874662-(2-{3-[2-(4-Benzyloxyphenyl)-5-methyl-1H-pyrrol-1-yl]propoxy}phenyl)-1,3-benzoxazoleAusbeute 59,4 %

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), 2-(2-hydroxyphenyl)benzoxazole (986 mg, 4.67 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=7:1) to give the object compound as an oily substance. 950 mg (yield: 59.4%)

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=7:1)
  5. customto give the object compound as an oily substance

Quellen und Nachweise

ORD-Eintrag
ord-169a0c9ad21c44739e5b54008a5136b0
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911468B2

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