Chlorine → 1H-inden-1-one

HRID 355363

Reaktionsgleichung

Reaktionsgleichung von HRID 355363
[O:1]1[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3](O)[C:2]1=2.ClCl.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>>[C:10]1(=[O:1])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

4

Edukt 3

HCID 24526ChlorineHCID 2724130Cornforth reagentHCID 54140692Epoxy indenol

Produkt 1

HCID 118153841H-inden-1-oneAusbeute 97,4 %

Versuchsvorschrift

To a solution of epoxy indenol 6 (0.24 g, 1.42 mmol) in 40 mL of CH2 Cl2, were added 2.16 g of oven dried Celite and PDC (2.16 g, 4 eq) at rt. After stirring at rt for 18 hr, the mixture was passed through 2 cm of flash silica gel pad, washed with 5% MeOH in CH2Cl2 (50 mL). The filtrate was concentrated and chromatographed with 35% EtOAc in hexane to give 0.18 g (75%) of indene-1-one 7 as colorless oil. The compound was identical with the literature by NMR (A. R. Daniewski; J. Kiegoel, J. Org. Chem. 1988, 53, 5534-5535).

Aufarbeitung

  1. washwashed with 5% MeOH in CH2Cl2 (50 mL)
  2. concentrationThe filtrate was concentrated
  3. customchromatographed with 35% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-38edae65710344859c79c3d3b101ca73
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05830885

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