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

HRID 404276

반응식

HRID 404276 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[H-].[Na+].[C:18]([O:23][CH3:24])(=[O:22])[CH:19]1[O:21][CH2:20]1>CN(C=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:20][CH:19]([OH:21])[C:18]([O:23][CH3:24])=[O:22])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 145751Methyl oxirane-2-carboxylateHCID 2748743,6-Dibromocarbazole

생성물 1

HCID 58097196Methyl 3-(3,6-Dibromo-9H-carbazol-9-yl)-2-hydroxypropanoate수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  1. stirringthe reaction was stirred
  2. temperaturewarmed to ambient temperature over 3.5 h
  3. customUpon completion by TLC the reaction mixture was partitioned between EtOAc and H2O
  4. extractionThe aqueous layer was extracted 3× with EtOAc
  5. washthe combined organics were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by chromatography (SiO2, 0-30% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-e6773ff2c4194e569cc90f99a88d8980
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748473B2

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