Diisopropylamine → 6-[2-cyclopentyl-4-(3-fluoro-4-isopropylphenyl)-2-hydroxybut-3-ynyl]-2,2-dimethyl-4H-1,3-dioxin-4-one

HRID 858589

Reaktionsgleichung

Reaktionsgleichung von HRID 858589
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[C:4]([F:11])[CH:3]=1.[CH:12]1([C:17]([OH:30])([C:28]#[CH:29])[CH2:18][C:19]2[O:24][C:23]([CH3:26])([CH3:25])[O:22][C:21](=[O:27])[CH:20]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(NC(C)C)(C)C>CN(C=O)C.CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:12]1([C:17]([OH:30])([C:28]#[C:29][C:2]2[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[C:4]([F:11])[CH:3]=2)[CH2:18][C:19]2[O:24][C:23]([CH3:26])([CH3:25])[O:22][C:21](=[O:27])[CH:20]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

8

Edukt 3

HCID 7912DiisopropylamineHCID 210510924-Bromo-2-fluoro-1-(1-methylethyl)benzeneHCID 224998026-(2-Cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one

Produkt 1

HCID 587625876-[2-cyclopentyl-4-(3-fluoro-4-isopropylphenyl)-2-hydroxybut-3-ynyl]-2,2-dimethyl-4H-1,3-dioxin-4-oneAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

4-Bromo-2-fluoro-1-isopropylbenzene (5.0 g, 23.2 mmol), 6-(2-cyclopentyl-2-hydroxybut-3-ynyl)-2,2-dimethyl-4H-1,3-dioxin-4-one (5.56 g, 21.0 mmol) were dissolved in anhydrous DMF (30 mL). To this solution, CuI (120 mg, 0.63 mmol), Pd(PPh3)2Cl2 (0.59 g, 0.84 mmol), and diisopropylamine (60 mL), were added sequentially. The mixture was then heated at 90° C. for 20 min before it was cooled down to 25° C. The reaction was diluted with EtOAc (150 mL) and washed with aqueous NH4Cl, brine, and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (040% EtOAc in hexanes) to give the desired product (7.5 g, 81% yield).

Aufarbeitung

  1. temperaturewas cooled down to 25° C
  2. washwashed with aqueous NH4Cl, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash column chromatography (040% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2caacc4625404161ba0665d00f684cee
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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