Reaction #685005

Reaction equation

3-(2-(1-benzothiophene-4-yl)ethoxy)-1-propanol

thionyl chloride

N,N-dimethylformamide

→

yellow oil

4-(2-(3-chloropropoxy)ethyl)-1-benzothiophene

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturethe obtained mixture was then heated
2. 2
   Temperatureto reflux for 5 hours
3. 3
   workup.DISTILLATIONSubsequently, the solvent was distilled away under a reduced pressure
4. 4
   OtherThe residue was purified by column chromatography (eluent; hexane:ethyl acetate=20:1)

Procedure

1.40 g of 3-(2-(1-benzothiophene-4-yl)ethoxy)-1-propanol was dissolved in 7.0 ml of methylene chloride. Thereafter, 1.10 ml of thionyl chloride and 0.05 ml of N,N-dimethylformamide were added to the obtained solution, and the obtained mixture was then heated to reflux for 5 hours. Subsequently, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; hexane:ethyl acetate=20:1), so as to obtain 1.43 g of a yellow oil product, 4-(2-(3-chloropropoxy)ethyl)-1-benzothiophene.

Source