반응 #43903

반응 방정식

4-bromo-3,5-dimethylphenol

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

Tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

수율 86.6%

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

수율 86.6%

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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.

출처