Reaktion #74798

Reaktionsgleichung

n-butyl lithium

1-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]-azepin-2-one

dimethyl disulfide

→

1-methylthiomethyl-3,4,5,5a,6,7-hexahydro9-methoxy-2H-naphth[1,2-d]azepin-2-one

Lösungsmittel

hexane

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe starting material is prepared
2. 2
   Temperaturcooled in a dry ice-acetone bath
3. 3
   workup.STIRRINGthe mixture stirred
4. 4
   Temperaturwith said cooling for 2 hours
5. 5
   SonstigeIt is quenched by the slow addition of 150 ml of water
6. 6
   Extraktionthe mixture is extracted with chloroform
7. 7
   Sonstigethe extract is dried
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue is crystallized from diethyl ether
10. 10
    Sonstigerecrystallized from ethyl acetate

Vorschrift

The starting material is prepared as follows: 36.4 ml of 2.5 M n-butyl lithium in hexane are added dropwise under nitrogen and at room temperature to the stirred suspension of 7.8 g of 1-methyl-9-methoxy-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]-azepin-2-one in 70 ml of anhydrous tetrahydrofuran. The mixture is stirred at room temperature for 45 minutes and cooled in a dry ice-acetone bath. The solution of 5.45 ml of dimethyl disulfide in 60 ml of tetrahydrofuran is added dropwise and the mixture stirred with said cooling for 2 hours. It is quenched by the slow addition of 150 ml of water, the mixture is extracted with chloroform, the extract is dried and evaporated. The residue is crystallized from diethyl ether and recrystallized from ethyl acetate, to give the 1-methylthiomethyl-3,4,5,5a,6,7-hexahydro9-methoxy-2H-naphth[1,2-d]azepin-2-one melting at 182°-184°.

Quelle