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

HRID 397858노트

반응식

HRID 397858 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
35 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c27b8bd615f453daa0a829294efdf96
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610728B2

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