Tricyclohexylphosphine → 2,3-Dihydro-5-[4-(phenylmethoxy)phenyl]-1H-inden-1-one

HRID 1352202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352202
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[CH2:23][CH2:22]2.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[F-].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[O:28])[CH2:23][CH2:22]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 75806TricyclohexylphosphineHCID 5206955-Bromo-1-indanoneHCID 522689Potassium FluorideHCID 27343144-Benzyloxy-phenylboronic acid

Produkt 1

HCID 211000302,3-Dihydro-5-[4-(phenylmethoxy)phenyl]-1H-inden-1-oneAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 4-benzyloxyphenyl boronic acid (0.15 g, 0.66 mmol), 5-bromo-1-indanone (0.10 g, 0.44 mmol), palladium acetate (2.0 mg, 0.009 mmol), tricyclohexylphosphine (7.0 mg, 0.018 mmol) and potassium fluoride (0.077 g, 1.32 mmol) in dioxane (2.5 mL) was stirred at 75° C. for 3 h. The reaction mixture was filtered through celite. Silica gel chromatography eluting with 25% ethyl acetate/hexane gave 0.05 g of desired product: 1H NMR (500 MHz, CDCl3) δ 7.85 (d, J=8.0 Hz, 1H), 7.68 (s, 1H), 7.62 (t, 3H), 7.51 (d, J=7.3 Hz, 2H), 7.46 (t, J=7.5 Hz, 2H), 7.38–7.42 (m, 1H), 7.13 (d, J=8.7 Hz, 2H), 5.18 (s, 2H), 3.23 (t, J=5.8 Hz, 2H), 2.78 (t, J=6.0 Hz, 2H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. washSilica gel chromatography eluting with 25% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2e24334c459c46f6a89d408fe879391b
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220734B2

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