反応 #9440

反応方程式

(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

溶媒

THF

反応条件

後処理

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

実験手順

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.

出典