Реакция #595394

Уравнение реакции

3,6-Dibromocarbazole

NaH

Methyl glycidate

→

desired product

Выход 32.0%

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

Выход 32.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction was stirred
2. 2
   Температураwarmed to ambient temperature over 3.5 h
3. 3
   ДругоеUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
4. 4
   ЭкстракцияThe aqueous layer was extracted 3× with EtOAc
5. 5
   Промывкаthe combined organics were washed with saturated aqueous NaCl
6. 6
   Сушкаdried over Na2SO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated in vacuo
9. 9
   ДругоеThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Методика

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%).

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