تفاعل #595394

معادلة التفاعل

3,6-Dibromocarbazole

NaH

Methyl glycidate

→

desired product

المردود 32.0%

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

المردود 32.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction was stirred
2. 2
   درجة الحرارةwarmed to ambient temperature over 3.5 h
3. 3
   أخرىUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
4. 4
   استخلاصThe aqueous layer was extracted 3× with EtOAc
5. 5
   غسيلthe combined organics were washed with saturated aqueous NaCl
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

الإجراء التجريبي

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%).

المصدر