Реакция #9785

Уравнение реакции

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

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was evaporated
2. 2
   СушкаThe organic phase was dried over magnesium sulfate
3. 3
   ДругоеThe product isolated
4. 4
   Другоеafter evaporation of the solvent
5. 5
   Другоеwas further purified by flash column chromatography

Методика

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.

Источник