Propargyl bromide → 6-(Prop-2-ynyloxy)isoindolin-1-one

HRID 1727399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727399
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]#[CH:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][NH:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[C:13]#[CH:12]

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 115283646-Hydroxy-2,3-dihydro-1H-isoindol-1-one

Produkt 1

HCID 575676686-(Prop-2-ynyloxy)isoindolin-1-oneAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The mixture of 6-hydroxyisoindolin-1-one ((73), 5.1 g, 34.2 mmol), propargyl bromide (80% solution in toluene, 5.70 ml, 51.3 mmol) K2CO3 (9.44 g, 68.4 mmol), KI (1.14 g, 6.8 mmol) in acetone was refluxed for overnight. The reaction mixture was filtered under vacuum and concentrated in vacuo to give the title compound (4.4 g, 68%) as a solid. MS (ES) m/z 188.1.

Aufarbeitung

  1. temperaturewas refluxed for overnight
  2. filtrationThe reaction mixture was filtered under vacuum
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bcb62e825c2e4866a919ef87ce5458ec
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495111B2

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