Réaction #9440

Équation de réaction

(4-Mercapto-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester

Triphenylphosphine

ADDP

3,3-bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-ol

→

{4-[3,3-bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction was stirred for further 2 h at 0° C
2. 2
   AutreThe reaction mixture was evaporated
3. 3
   Autrethe residue was triturated with ether (2×15 ml)
4. 4
   AutreThe filtered ether phases were evaporated
5. 5
   Autrepurified by column chromatography (eluent: ethyl acetate)

Mode opératoire

Triphenylphosphine (138 mg, 0.68 mmol) and ADDP (173 mg, 0.68 mmol) were added to a solution of 3,3-bis-(4-pyridin-3-yl-phenyl)-prop-2-en-1-ol (100 mg, 0.27 mmol) in THF (5 ml) at 0° C. The reaction mixture was stirred for 5 min under nitrogen atmosphere. (4-Mercapto-2-trifluoromethyl-phenoxy)-acetic acid ethyl ester (prepared analogous to procedure in BioOrg. Med. Chem. Lett. 2003, 13, 1517) (92 mg, 0.32 mmol) was slowly added to the reaction mixture and the reaction was stirred for further 2 h at 0° C. The reaction mixture was evaporated and the residue was triturated with ether (2×15 ml). The filtered ether phases were evaporated and purified by column chromatography (eluent: ethyl acetate) to give {4-[3,3-bis-(4-pyridin-3-yl-phenyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester in 100 mg (60%) yield.

Source