反応 #360604

反応方程式

ethyl 3-{2-fluoro-4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

収率 91.0%

ethyl 3-(4-{[2′,6′-dimethyl-4′-(tetrahydro-2H-thiopyran-4-yloxy)biphenyl-3-yl]methoxy}-2-fluorophenyl)propanoate

収率 91.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 19 hrs
2. 2
   workup.STIRRINGThe mixture was further stirred at the same temperature for 6 hrs
3. 3
   濃縮The reaction mixture was concentrated under reduced pressure
4. 4
   その他the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1)

実験手順

To a solution of ethyl 3-{2-fluoro-4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate (0.50 g, 1.18 mmol), tetrahydro-2H-thiopyran-4-ol (0.15 g, 1.30 mmol) and triphenylphosphine (0.31 g, 1.30 mmol) in tetrahydrofuran (10 mL) was added diethyl azodicarboxylate (40% toluene solution, 0.70 mL, 1.53 mmol) at room temperature with stirring. The reaction mixture was stirred at room temperature for 19 hrs., and an equivalent amount of the aforementioned reagents (tetrahydro-2H-thiopyran-4-ol, triphenylphosphine and diethyl azodicarboxylate) were added. The mixture was further stirred at the same temperature for 6 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1) to give the title compound (0.53 g, yield 91%) as a yellow oil.

出典