Reaktion #9785

Reaktionsgleichung

tributylphosphine

ethyl(4-mercapto-2-methylphenoxy)acetate

{5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol

→

title compound

ethyl{2-methyl-4-[({5-[4-(trifluoromethyl)phenyl]-3-furyl}methyl)thio]phenoxy}acetate

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   TrocknenThe organic phase was dried over magnesium sulfate
3. 3
   SonstigeThe product isolated
4. 4
   Sonstigeafter evaporation of the solvent
5. 5
   Sonstigewas further purified by flash column chromatography

Vorschrift

A solution of {5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (0.15 g) in tetrahydrofuran (15 ml) stirred at 0° C. was treated with tributylphosphine (0.2 ml), as solution of ethyl(4-mercapto-2-methylphenoxy)acetate (0.150 g) in tetrahydrofuran (2 ml) and finally azodicarbonyldimorpholide (0.204 g). The reaction was allowed to warm to ambient temperature and stirred for 18 hours. The solvent was evaporated and the residue subjected to an aqueous work up using ethyl acetate and water. The organic phase was dried over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using a cyclohexane:ethyl acetate (5:1) as eluent to give the title compound.

Quelle