Reaction #9749

Reaction equation

ethyl(4-hydroxy-2-methylphenoxy)acetate

intermediate 7

ethyl(4-hydroxy-2-methylphenoxy)acetate

2-(2-thienyl)ethanol

tri-n-butyl phosphine

→

title compound

ethyl[2-methyl-4-(2-thien-2-ylethoxy)phenoxy]acetate

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated
2. 2
   Otherthe residue partitioned between ethyl acetate and water
3. 3
   OtherThe organic layer was collected
4. 4
   Dryingdried over sodium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Otherthe residue purified by SPE (Si cartridge)
7. 7
   Washeluting with cyclohexane:ethyl acetate (20:1)

Procedure

A solution of ethyl(4-hydroxy-2-methylphenoxy)acetate (intermediate 7, 1.05 g) and 2-(2-thienyl)ethanol (0.64 g) in dry tetrahydrofuran was treated with tri-n-butyl phosphine (1.2 g) and azodicarbonyldimorpholide (1.53 g) and the mixture stirred at ambient temperature for 3 days. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, concentrated and the residue purified by SPE (Si cartridge) eluting with cyclohexane:ethyl acetate (20:1) to give the title compound as a colourless oil.

Source