Reacción #9440

Ecuación de reacción

(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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente