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

HRID 62182

反応式

HRID 62182 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5388e97b41d842b3a71dd7168ec57a11
出典データセット
uspto-grants-2016_09
特許番号
US09446042B2

関連ノート

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