Reaktion #1996049

Reaktionsgleichung

4-bromo-3,5-dimethylphenol

tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

Tetrahydro-2H-thiopyran-4-ol

triphenylphosphine

diethyl azodicarboxylate

→

title compound

Ausbeute 86.6%

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

Ausbeute 86.6%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle