Ammonium Chloride → 2-tert-Butyl-1H-indole

HRID 73918

반응식

HRID 73918 반응식
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=O.[Li]CCCC.[NH4+].[Cl-]>C1COCC1>[C:2]([C:3]1[NH:5][C:6]2[C:7]([CH:12]=1)=[CH:8][CH:9]=[CH:10][CH:11]=2)([CH3:14])([CH3:13])[CH3:1]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 27340052,2,2'-TrimethylpropionanilideHCID 178418339Butyllithium

생성물 1

HCID 5941662-tert-Butyl-1H-indole수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
15 °C

실험 절차

To a solution of 2,2-dimethyl-N-o-tolyl-propionamide (30.0 g, 159 mmol) in dry THF (100 mL) was added dropwise n-BuLi (2.5 M, in hexane, 190 mL) at 15° C. The mixture was stirred overnight at 15° C., cooled in an ice-water bath and treated with saturated NH4Cl solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography to give 2-tert-butyl-1H-indole (23.8 g, 88%).

후처리

  1. temperaturecooled in an ice-water bath
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-4ca182b4ca6d488e8563b7fa18beedc3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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