Reaction #725437

Reaction equation

4-(4-hydroxyphenyl)pentanol

potassium carbonate

methyl 3-bromomethyl-2-thiophenecarboxylate

→

product

Yield 75.7%

4-[4-(2-Carbomethoxy-3-thienylmethoxy)phenyl]pentanol

Yield 75.7%

Solvents

2-butanone

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux overnight, with exclusion of moisture
3. 3
   FiltrationThe mixture was filtered while hot and the filter cake
4. 4
   Washwas washed with 2-butanone
5. 5
   ConcentrationThe combined filtrate was concentrated
6. 6
   Washa solution of the residue and dichloromethane was washed with 10% sodium hydroxide solution, water and saturated brine
7. 7
   DryingThe dried (over anhydrous sodium sulfate) organic phase
8. 8
   Filtrationwas filtered
9. 9
   Concentrationthe filtrate was concentrated to an oil
10. 10
    OtherPurification by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; two silica gel columns; 0.2 l/min flow rate; Gow Mac model 80-800 UV detector; 30% V/V ethyl acetate in hexane)

Procedure

A stirred suspension of 8.0 g of 4-(4-hydroxyphenyl)pentanol, 18.41 g of anhydrous potassium carbonate, 0.4 g of potassium iodide, 10.44 g of methyl 3-bromomethyl-2-thiophenecarboxylate, and 225 ml of 2-butanone was heated under reflux overnight, with exclusion of moisture. The mixture was filtered while hot and the filter cake was washed with 2-butanone. The combined filtrate was concentrated, and a solution of the residue and dichloromethane was washed with 10% sodium hydroxide solution, water and saturated brine. The dried (over anhydrous sodium sulfate) organic phase was filtered and the filtrate was concentrated to an oil. Purification by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; two silica gel columns; 0.2 l/min flow rate; Gow Mac model 80-800 UV detector; 30% V/V ethyl acetate in hexane) gave 11.23 g (75.6%) of product as an oil, dried at 60° C. for 2 hours.

Source