반응 #9440

반응 방정식

(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

용매

THF

반응 조건

후처리

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

실험 절차

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.

출처