反応 #595394

反応方程式

3,6-Dibromocarbazole

NaH

Methyl glycidate

→

desired product

収率 32.0%

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

収率 32.0%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction was stirred
2. 2
   温度warmed to ambient temperature over 3.5 h
3. 3
   その他Upon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
4. 4
   抽出The aqueous layer was extracted 3× with EtOAc
5. 5
   洗浄the combined organics were washed with saturated aqueous NaCl
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

実験手順

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%).

出典