Triethylamine → 4-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

HRID 546858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546858
C(N(CC)CC)C.[C:8]([C:10]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11]1)#[CH:9].[CH2:16]([C:18]([C:29]1[CH:34]=[CH:33][C:32](OS(C(F)(F)F)(=O)=O)=[C:31]([CH3:43])[CH:30]=1)([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)[CH2:19][CH3:20])[CH3:17].C(OCC)(=O)C>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([C:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[CH:22]=1)([C:29]1[CH:34]=[CH:33][C:32]([C:9]#[C:8][C:10]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11]2)=[C:31]([CH3:43])[CH:30]=1)[CH2:19][CH3:20])[CH3:17]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 870741-EthynylcyclopentanolHCID 58598300Trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester

Produkt 1

HCID 574833964-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenolAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Triethylamine (5.2 mL, 37.3 mmol), 1-ethynylcyclopentanol (2 g, 18.2 mmol), cuprous iodide (0.24 g, 1.26 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.44 g, 1.25 mmol) were added to a solution of trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester (Example 1-(1); 5.2 g, 12.5 mmol) in acetonitrile (52 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred at 110° C. for four hours. Ethyl acetate was added to the residue. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=4/1) to give the title compound (3 g, 64%).

Aufarbeitung

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-845aa288cf8c49c991f45d790fb81d9c
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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