反応 #74798

反応方程式

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

溶媒

hexane

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他The starting material is prepared
2. 2
   温度cooled in a dry ice-acetone bath
3. 3
   workup.STIRRINGthe mixture stirred
4. 4
   温度with said cooling for 2 hours
5. 5
   その他It is quenched by the slow addition of 150 ml of water
6. 6
   抽出the mixture is extracted with chloroform
7. 7
   その他the extract is dried
8. 8
   その他evaporated
9. 9
   その他The residue is crystallized from diethyl ether
10. 10
    その他recrystallized from ethyl acetate

実験手順

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°.

出典