Reaktion #90424

Reaktionsgleichung

3,6-Dibromocarbazole

NaH

Methyl glycidate

→

desired product

Ausbeute 32.0%

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

Ausbeute 32.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred
2. 2
   Temperaturwarmed to ambient temperature over 3.5 h
3. 3
   SonstigeUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
4. 4
   ExtraktionThe aqueous layer was extracted 3× with EtOAc
5. 5
   Waschenthe combined organics were washed with saturated aqueous NaCl
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Vorschrift

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%).

Quelle