Reaktion #1997023

Reaktionsgleichung

2-methoxythiophene

n-C11H23OH

toluene

p-toluenesulfonic acid monohydrate

→

2-undecanoxy-thiophene

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux under nitrogen for 19 hours
3. 3
   Extraktionthe mixture was extracted with dichloromethane (DCM, 250 mL)
4. 4
   WaschenThe organic layer was washed with water and brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated in vacuo

Vorschrift

A mixture of 2-methoxythiophene (5.13 g, 44.93 mmol), n-C11H23OH (15.5 g, 89.87 mmol), toluene (50 mL), and p-toluenesulfonic acid monohydrate (0.85 g, 4.47 mmol) was heated to reflux under nitrogen for 19 hours. After cooling to room temperature, the reaction mixture was poured into water (150 mL), and the mixture was extracted with dichloromethane (DCM, 250 mL). The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue was subjected to flash column on silica gel with hexane as eluent (slowly up to a hexane:DCM (8:2, v/v) mixture), leading to a colorless oil as the product (7.76 g, 67.9%).

Quelle