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

HRID 397858ノート

反応式

HRID 397858 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) is added to 7.82 g (24 mmol) cesium carbonate in 25 mL DMF and the mixture is 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 is added and stirring maintained until the reaction is judged complete by TLC analysis (several hours). The mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 6.8 g of solid.

後処理

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

出典と根拠

ORDレコード
ord-1c27b8bd615f453daa0a829294efdf96
出典データセット
uspto-grants-2003_08
特許番号
US06610728B2

反応ノート

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