2,6-Lutidine → 4-[1,3]Dioxan-2-yl-benzenethiol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

2-(4-Methanesulfinyl-phenyl)-[1,3]dioxane (400 mg, 1.76 mmol) is dissolved in acetonitrile (20 mL). 2,6-Lutidine (0.64 mL, 5.5 mmol) is added and the solution is cooled to −10° C. TFAA (0.75 mL, 5.3 mmol) is added dropwise via syringe. The reaction is stirred for 1 h at −10 to 0° C. All volatile materials are evaporated while keeping the reaction mixture at 0° C. A mixture of MeOH and triethyl amine (50 mL, 1:1 v/v) that has been pre-cooled to 0° C. is added. The resulting mixture is allowed to warm and stir at room temperature for 30 min. All volatile materials are evaporated. The obtained residue is dissolved in diethyl ether and washed with saturated aqueous NH4Cl. The organic layer is separated, dried over Na2SO4, and concentrated to give crude 4-[1,3]dioxan-2-yl-benzenethiol as a yellow oil, which is used immediately in the next step without further purification.

Herkunft & Nachweise