Tributylphosphine → 3-(4-{1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester

HRID 860675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860675
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:16]([OH:18])[CH3:17])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:50][O:51][C:52](=[O:63])[CH2:53][CH2:54][C:55]1[CH:60]=[CH:59][C:58](O)=[CH:57][C:56]=1[CH3:62]>C1(C)C=CC=CC=1>[CH3:50][O:51][C:52](=[O:63])[CH2:53][CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:18][CH:16]([C:10]2[O:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH:13]([CH3:15])[CH3:14])[CH3:17])=[CH:57][C:56]=1[CH3:62]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoateHCID 587656641-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol

Produkt 1

HCID 101521383-(4-{1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl esterAusbeute 80,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1-[2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol (9.05 g, 29.2 mmol) in toluene (300 ml) at 0° C. is added tri-n-butylphosphine (7.70 g, 38.1 mmol) and 1,1′-(azodicarbonyl)-dipiperidine (8.84 g, 35.0 mmol), followed by addition of 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (6.30 g, 32.1 mmol). The resulting mixture is stirred for 18 hours while warmed up to room temperature. The reaction is quenched with water (100 ml) and the aqueous layer is extracted with EtOAc (2×100 ml). The combined organics are dried over Na2SO4 and concentrated, purified by silica gel chromatography (Hexanes/EtOAc, 9/1 to 8.5/1.5) to afford the 3-(4-{1-[2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester as a colorless oil (11.4 g, 80%). MS (MH+): 488.1.

Aufarbeitung

  1. customThe reaction is quenched with water (100 ml)
  2. extractionthe aqueous layer is extracted with EtOAc (2×100 ml)
  3. dry with materialThe combined organics are dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (Hexanes/EtOAc, 9/1 to 8.5/1.5)

Quellen und Nachweise

ORD-Eintrag
ord-c11460d8731d4ce0b09b859d5c024e73
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153878B2

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