Reaktion #50876

ord-587e58b6fba14d42ba8d726ca562288a

Reaktionsgleichung

Clc1ccc2ccc(C3CC3c3cccc(C4OCCO4)c3)nc2c1
dioxolane
Clc1ccc2ccc(C3CC3c3cccc(C4OCCO4)c3)nc2c1
2-(3-(2-(7-chloroquinolin-2-yl)cyclopropyl)phenyl)1,3-dioxolane
CCOC(C)=O
EtOAc
→
O=Cc1cccc(C2CC2c2ccc3ccc(Cl)cc3n2)c1
title compound
O=Cc1cccc(C2CC2c2ccc3ccc(Cl)cc3n2)c1
3-(2-(7-chloroquinolin-2-yl)cyclopropyl)benzaldehyde

Edukte

Clc1ccc2ccc(C3CC3c3cccc(C4OCCO4)c3)nc2c1
dioxolane
Clc1ccc2ccc(C3CC3c3cccc(C4OCCO4)c3)nc2c1
2-(3-(2-(7-chloroquinolin-2-yl)cyclopropyl)phenyl)1,3-dioxolane
—
NH4OAc
CCOC(C)=O
EtOAc

Reagenzien

Keine

Lösungsmittel

C1CCOC1.CC(=O)O.O
THF AcOH H2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigedrying
  2. 2
    Sonstigeevaporation, and flash chromatography on silica with EtOAc:toluene 2.5:97.5

Vorschrift

The dioxolane (step 3) (500 mg, 1.42 mmoles) was heated at reflux in 9 mL of THF:AcOH:H2O 6:2:1 for 2 hours. Addition of 25% NH4OAc, extraction with EtOAc, drying, evaporation, and flash chromatography on silica with EtOAc:toluene 2.5:97.5 afforded the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05428171uspto-grants-1995_06