Reacción #60382

Ecuación de reacción

DBU

trifluoro-methanesulfonic acid 5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl ester

trifluoro-methanesulfonic acid 5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl Ester

DPPA

→

title compound

trifluoro-methanesulfonic acid 5-azido-5,6,7,8-tetrahydro-naphthalen-2-yl Ester

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was warmed to RT
2. 2
   ConcentraciónThe mixture was concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in EtOAc (400 mL)
4. 4
   Lavadowashed with saturated NH4Cl (twice), H2O, and brine
5. 5
   Secadodried over Na2SO4
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude was purified by flash chromatography (5% EtOAc-hexane)

Procedimiento

To a solution of trifluoro-methanesulfonic acid 5-hydroxy-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Step B, 11.2 g, 37.9 mmol, 1.0 eq) in THF (150 mL) at RT was added DPPA (Aldrich, 11.1 mL, 51.6 mmol, 1.36 eq). The resulting mixture was cooled to 0° C. and then DBU (Aldrich, 7.7 mL, 51.6 mmol, 1.36 eq) was added slowly through a syringe. The reaction was warmed to RT and stirred over the weekend. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc (400 mL), washed with saturated NH4Cl (twice), H2O, and brine, dried over Na2SO4 and concentrated in vacuo. The crude was purified by flash chromatography (5% EtOAc-hexane) to provide the title compound.

Fuente