反応 #43903

反応方程式

4-bromo-3,5-dimethylphenol

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

Tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

収率 86.6%

4-(4-bromo-3,5-dimethylphenoxy)tetrahydro-2H-thiopyran

収率 86.6%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was further stirred for 1.5 hr
2. 2
   濃縮The reaction mixture was concentrated under reduced pressure
3. 3
   その他the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

実験手順

To a solution of 4-bromo-3,5-dimethylphenol (0.201 g, 1.00 mmol), tetrahydro-2H-thiopyran-4-ol (0.130 g, 1.10 mmol) and triphenylphosphine (0.341 g, 1.30 mmol) in tetrahydrofuran (5 mL) was added diethyl azodicarboxylate (40% solution in toluene, 0.591 mL, 1.30 mmol), and the mixture was stirred at room temperature for 1.5 hr. Tetrahydro-2H-thiopyran-4-ol (0.0591 g, 0.500 mmol), triphenylphosphine (0.157 g, 0.600 mmol) and diethyl azodicarboxylate (40% solution in toluene, 0.272 mL, 0.600 mmol) were added, and the mixture was further stirred for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (0.261 g, yield 86%) as colorless crystals.

出典