Reaktion #75085

ord-2e349f16a0ab4c7baaf37321e4e4dae6

Reaktionsgleichung

C=C[C@H]1CN2CCC1C[C@@H]2[C@@H](O)c1ccnc2ccc(OC)cc12
quinidine
O=C1C=CC=C2C1=Cc1ccccc12
fluorenone
[Na]
sodium
→
C=C[C@H]1CN2CC[C@H]1C[C@@H]2C(=O)c1ccnc2ccc(OC)cc12
quinidinone

Edukte

C=C[C@H]1CN2CCC1C[C@@H]2[C@@H](O)c1ccnc2ccc(OC)cc12
quinidine
O=C1C=CC=C2C1=Cc1ccccc12
fluorenone
[Na]
sodium

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene
Cc1ccccc1
toluene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONby mixing 9 g
  2. 2
    workup.ADDITIONTo this solution was added a hot solution of 37 g
  3. 3
    TemperaturAfter 15 minutes at reflux
  4. 4
    ExtraktionAfter extraction and neutralization treatments as in Example I, 36 g

Vorschrift

A solution of fluorenone ketyl was prepared by mixing 9 g. of fluorenone and 6.5 g. of sodium in anhydrous toluene. To this solution was added a hot solution of 37 g. of anhydrous quinidine base in 150 ml. of anhydrous toluene. After 15 minutes at reflux, the reaction was complete. After extraction and neutralization treatments as in Example I, 36 g. of pure quinidinone (TLC) was obtained (97% of theory).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04175192uspto-grants-1979_11