Réaction #9785

Équation de réaction

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

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated
2. 2
   SéchageThe organic phase was dried over magnesium sulfate
3. 3
   AutreThe product isolated
4. 4
   Autreafter evaporation of the solvent
5. 5
   Autrewas further purified by flash column chromatography

Mode opératoire

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.

Source