Reaktion #310357

Reaktionsgleichung

ether

sodium hydride

cis-7-chloro-3-hydroxy-2,3-dihydro-2-(1'-imidazolylmethyl)benzo(b)thiophene

chloromethyl methyl sulfide

→

cis-7-chloro-3-(methylthiomethoxy)-2,3-dihydro-2-(1'-imidazolylmethyl)benzo(b)-thiophene

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextract with three portions (500 ml
2. 2
   TrocknenDry the ether solution over anhydrous magnesium sulfate
3. 3
   Sonstigeevaporate in vacuo
4. 4
   Wascheneluting with ethyl acetate
5. 5
   Sonstigeevaporate the combined residues

Vorschrift

To a suspension of cis-7-chloro-3-hydroxy-2,3-dihydro-2-(1'-imidazolylmethyl)benzo(b)thiophene (2.67 gms., 10 mmols) in dry dimethylformamide (30 ml.) at 0°-5° C., add sodium hydride (50% oil dispersion) (0.53 gms., 11 mmols) and stir for one hour at room temperature. Add chloromethyl methyl sulfide (1.06 gms., 11 mmols) and stir again for one hour at room temperature. Pour the reaction mixture into ether (500 ml.) and extract with three portions (500 ml. each) of water. Dry the ether solution over anhydrous magnesium sulfate and evaporate in vacuo. Chromatograph the resultant residue by high pressure liquid chromatography using two silica gel cartridges and eluting with ethyl acetate. Combine the like eluates as determined by thin layer chromatography and evaporate the combined residues to give cis-7-chloro-3-(methylthiomethoxy)-2,3-dihydro-2-(1'-imidazolylmethyl)benzo(b)-thiophene.

Quelle