Cesium carbonate → tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

HRID 1280815ノート

反応式

HRID 1280815 の反応式
[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C=O)C.O>[C:31]([O:30][C:28](=[O:29])[CH2:27][O:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:3]([CH2:1][CH3:2])[N:4]2[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:34])([CH3:33])[CH3:32]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 98164161-Benzyl-2-ethyl-1H-indol-4-OL

生成物 1

HCID 12015898tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
35 °C

実験手順

2-Ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (5.82 g, 20 mmol) was added to 7.82 g (24 mmol) cesium carbonate in 25 mL DMF and the mixture stirred at 35° C. for 30 minutes. After cooling to 20° C., a solution of tert-butyl bromoacetate (4.65 g, 23.8 mmol) in 5 mL DMF was added and stirring maintained until the reaction was judged complete by TLC analysis (several hours). The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 6.8 g of solid. Mass spectrum: 365

後処理

  1. temperatureAfter cooling to 20° C.
  2. stirringstirring
  3. temperaturemaintained until the reaction
  4. customwas judged complete by TLC analysis (several hours)
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated at reduced pressure

出典と根拠

ORDレコード
ord-bd2d314d894b4cb18901d38a0e32777e
出典データセット
uspto-grants-2002_09
特許番号
US06451839B1

反応ノート

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