Triethylamine → 1H-inden-1-one

HRID 1435768

Reaktionsgleichung

Reaktionsgleichung von HRID 1435768
C(N(CC)CC)C.Br[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[CH2:10]1>C1COCC1>[C:11]1(=[O:18])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:10]1

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 117459123-Bromo-1-indanone

Produkt 1

HCID 118153841H-inden-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (4.5 mL; 32 mmol; 1.2 equiv.) was added to 3-bromo-indan-1-one (5.6 g; 27 mmol) in 100 mL THF at 0° C. and stirred 1 h at r.t. The reaction mixture was filtered to remove triethylammonium bromide and concentrated in vacuo to give inden-1-one. 7-Fluoroindole (3.3 g, 22 mmol ) and Sc(OTf)3 (550mg, 5 mol %) were added to inden-1-one in 100 mL CH2Cl2 at 0° C. The reaction mixture was allowed to warm to room temperature over night. 100 mL ethyl acetate was added and the mixture was filtered through a silica gel plug and concentrated in vacuo. After flash chromatography (heptane/ethyl acetate, silica gel) 5.9 g 3-(7-fluoro-1H-indol-3-yl)-indan-1-one (82%) was isolated.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove triethylammonium bromide
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9552896c8753447fac0852623ae7a397
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618967B2

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