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

Temperatur

-10 °C

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.

1. customAll volatile materials are evaporated
2. customat 0° C
3. additionA mixture of MeOH and triethyl amine (50 mL, 1:1 v/v) that
4. temperaturehas been pre-cooled to 0° C.
5. additionis added
6. temperatureto warm
7. stirringstir at room temperature for 30 min
8. customAll volatile materials are evaporated
9. dissolutionThe obtained residue is dissolved in diethyl ether
10. washwashed with saturated aqueous NH4Cl
11. customThe organic layer is separated
12. dry with materialdried over Na2SO4
13. concentrationconcentrated

ORD-Eintrag

ord-fa520a8d4f4a492b8a00831ee6fc2b32

Quelldatensatz

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07060697B2