Dimethylformamide → 1-Indanone

HRID 496395

Reaktionsgleichung

Reaktionsgleichung von HRID 496395
OC1CC[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)C1=O.O[CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:23].C(Br)[CH:25]=[CH2:26].C([O-])([O-])=O.[Cs+].[Cs+].C[N:35](C=O)C>CCOCC>[CH3:26][CH2:25][N:35]([C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:22][CH3:14].[C:15]1(=[O:23])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:14]1

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 30140171H-Inden-1-one, 2,3-dihydro-2-hydroxy-HCID 110082362-Hydroxytetralin-1-one

Produkt 2

HCID 67351-IndanoneHCID 7061N,N-Diethylaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A commercially available hydroxy-tetralone or hydroxyindanone is treated with an allyl bromide in the presence of a base such as Cs2CO3 in a solvent such as DMF to afford the ether. Claisen rearrangement in a solvent such as diethylaniline affords the substituted tetralone or indanone. The Mitsunobu reaction then affords the 2-imidazolyl-1-R3-ethoxy)prop-2-enyl compound. Alternatively, the substituted tetralone or indanone is reduced with a catalyst such as RhCl(PPh3)3 in the presence of H2 neat to afford a (prop-2-enyl)phenol derivative. Mitsunobu reaction of the phenol the desired imidazole alcohol affords the 2-imidazolyl-1-R3-ethoxy prop-2-enyl tetralone or indanone derivative.

Quellen und Nachweise

ORD-Eintrag
ord-9e891cfdc18443b6a347177152bdea5b
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943183B2

Verknüpfte Notizen

Wird geladen…