Reaktion #9749

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   Sonstigethe residue partitioned between ethyl acetate and water
3. 3
   SonstigeThe organic layer was collected
4. 4
   Trocknendried over sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   Sonstigethe residue purified by SPE (Si cartridge)
7. 7
   Wascheneluting with cyclohexane:ethyl acetate (20:1)

Vorschrift

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.

Quelle