Sodium hydride → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

HRID 1427257ノート

反応式

HRID 1427257 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C.CCOC(C)=O>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH:15]([N:1]2[C:9]3[C:4](=[C:5]([CH:10]=[O:11])[CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[C:16]([O:18][CH3:19])=[O:17])=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 333703Indole-4-carboxaldehydeHCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetate

生成物 1

HCID 86705047methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1H-indole-4-carbaldehyde (2.0 g, 13.79 mmol) in DMF (50 mL) was added NaH (0.66 g, 16.55 mmol) at 0° C. After stirring for 30 min at 0° C., a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (4.67 g, 17.92 mmol) in DMF (20 mL) was added dropwise. The reaction was allowed to warm to rt and stirred for an additional 1 hr. Then it was diluted with EtOAc (200 mL) and quenched with water. The organic layer was separated and washed with brine (50 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-20% EtOAc/hexanes) to provide the title compound.

後処理

  1. temperatureto warm to rt
  2. stirringstirred for an additional 1 hr
  3. customquenched with water
  4. customThe organic layer was separated
  5. washwashed with brine (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified via column chromatography (0-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-8b48ad9519324559a723f178c789bb0c
出典データセット
uspto-grants-2015_01
特許番号
US08933113B2

反応ノート

読み込み中…