반응 #65699

반응 방정식

MeMgI

m-bromothiophenol

8-bromo-3,4-dihydro-1-benzothiepin-5(2H)-one

→

8-bromo-2,3,4,5-tetrahydro-5-methyl-1-benzothiepine

용매

ether

반응 조건

후처리

1. 1
   기타the resulting tertiary alcohol was deoxygenated
2. 2
   workup.ADDITIONtreated in succession with 75.1 g of sodium iodide (NaI), 26.4 ml of acetonitrile and 63.5 ml of Me3SiCl
3. 3
   workup.ADDITIONpoured on to ice
4. 4
   추출extracted with ether
5. 5
   세척washed with bisulfite solution and water
6. 6
   기타dried
7. 7
   기타evaporated

실험 절차

First, m-bromothiophenol was converted into 8-bromo-3,4-dihydro-1-benzothiepin-5(2H)-one. This ketone was methylated with MeMgI in ether and the resulting tertiary alcohol was deoxygenated as follows: 22.85 g were placed in 250 ml of hexane under argon and treated in succession with 75.1 g of sodium iodide (NaI), 26.4 ml of acetonitrile and 63.5 ml of Me3SiCl. The mixture was stirred at room temperature overnight, poured on to ice, extracted with ether, washed with bisulfite solution and water, dried and evaporated. Chromatography on silica gel with petroleum ether gave 18.1 g of 8-bromo-2,3,4,5-tetrahydro-5-methyl-1-benzothiepine as a pale yellow oil.

출처