Reaction #9785

Reaction equation

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

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherThe solvent was evaporated
2. 2
   DryingThe organic phase was dried over magnesium sulfate
3. 3
   OtherThe product isolated
4. 4
   Otherafter evaporation of the solvent
5. 5
   Otherwas further purified by flash column chromatography

Procedure

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