Reaction #357838

Reaction equation

2-thiopheneethanol

diisopropylamine

2-methoxyethoxymethyl chloride

→

title compound

Yield 85.0%

2-[2-(2-methoxyethoxymethoxy)ethyl]thiophene

Yield 85.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 2 hours
3. 3
   TemperatureThe reaction product solution was cooled
4. 4
   Concentrationconcentrated by evaporation under reduced pressure
5. 5
   workup.ADDITIONTo the residue, 200 mL of water and 250 mL of n-hexane were added
6. 6
   workup.STIRRINGthe resulting mixture was stirred for 5 minutes
7. 7
   Washthe organic layer was washed twice with 700 mL portions of water
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   Concentrationconcentrated under reduced pressure

Procedure

15.0 g of 2-thiopheneethanol was dissolved in 350 mL of dichloromethane, and 30.2 g of diisopropylamine was added thereto. The resulting mixture was cooled to 0° C. and 17.5 g of 2-methoxyethoxymethyl chloride was added thereto. The resulting mixture was stirred for 2 hours and heated to reflux for 2 hours. The reaction product solution was cooled and concentrated by evaporation under reduced pressure. To the residue, 200 mL of water and 250 mL of n-hexane were added, and the resulting mixture was stirred for 5 minutes. Aqueous layer was discarded, and the organic layer was washed twice with 700 mL portions of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 21.5 g (yield of 85%) of the title compound as a colorless oil.

Source