Reacción #595394

Ecuación de reacción

3,6-Dibromocarbazole

NaH

Methyl glycidate

→

desired product

Rendimiento 32.0%

Methyl 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate

Rendimiento 32.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction was stirred
2. 2
   Temperaturawarmed to ambient temperature over 3.5 h
3. 3
   OtroUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
4. 4
   ExtracciónThe aqueous layer was extracted 3× with EtOAc
5. 5
   Lavadothe combined organics were washed with saturated aqueous NaCl
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Procedimiento

3,6-Dibromocarbazole (0.300 g, 0.923 mmol) was dissolved in DMF (1.2 mL) and cooled to 0° C. NaH (60% dispersion in mineral oil, 0.074 g, 1.846 mmol) was added and the reaction stirred for 1 h at 0° C. Methyl glycidate (0.471 g, 4.615 mmol) was added and the reaction was stirred and warmed to ambient temperature over 3.5 h. Upon completion by TLC the reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted 3× with EtOAc, and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane) to afford the desired product (125 mg, 32%).

Fuente