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Potassium Phosphate, Tribasic → (4'-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

HRID 546893
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546893
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:50]([C:52]([OH:85])([CH2:83][CH3:84])[CH2:53][CH2:54][C:55]1[CH:60]=[CH:59][C:58]([C:61]([CH2:80][CH3:81])([C:64]2[CH:69]=[CH:68][C:67](B3OC(C)(C)C(C)(C)O3)=[C:66]([CH3:79])[CH:65]=2)[CH2:62][CH3:63])=[CH:57][C:56]=1[CH3:82])[CH3:51].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:67]2[CH:68]=[CH:69][C:64]([C:61]([CH2:62][CH3:63])([C:58]3[CH:59]=[CH:60][C:55]([CH2:54][CH2:53][C:52]([CH2:83][CH3:84])([OH:85])[CH2:50][CH3:51])=[C:56]([CH3:82])[CH:57]=3)[CH2:80][CH3:81])=[CH:65][C:66]=2[CH3:79])=[CH:7][CH:6]=1
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Komponenten

9

Edukt 5

HCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 577091063-Ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-pentan-3-ol

Produkt 1

HCID 57709110
(4'-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pentyl)-3-methyl-phenyl]-propyl}-2'-methyl-biphenyl-4-yl)acetic acid methyl ester
Ausbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(4-Bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 38.5 mg, 0.168 mmol), palladium acetate (2.5 mg, 0.011 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (9.0 mg, 0.022 mmol), potassium phosphate (71 mg, 0.336 mmol) and water (0.2 mL) were added to a solution of 3-ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-pentan-3-ol (Example 29; 55 mg, 0.112 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for 3.5 hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the target compound as a colorless oil (30.1 mg, 52%).

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-618502c262c34c539c340bf50f4d46db
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935688B2

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