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

HRID 468391

반응식

HRID 468391 반응식
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=O)[C:9]([CH3:12])([CH3:11])[CH3:10].[NH4+].[Cl-]>[Li]CCCC>[C:9]([C:8]1[NH:7][C:2]2[C:1]([CH:14]=1)=[CH:6][CH:5]=[CH:4][CH:3]=2)([CH3:12])([CH3:11])[CH3:10]

참가 물질

4

반응물 2

HCID 25517Ammonium ChlorideHCID 27340052,2,2'-Trimethylpropionanilide

생성물 1

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

시약·촉매·용매 1

HCID 178418339Butyllithium용매

반응 조건

온도
15 °C

실험 절차

To a solution of N-o-tolylpivalamide (30.0 g, 159 mmol) in dry THE (100 mL) was added dropwise n-BuLi (2.5 M in hexane, 190 mL) at 15° C. After addition, the mixture was stirred overnight at 15° C. The mixture was cooled in an ice-water bath and treated with saturated NH4Cl. 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 on silica gel to give 2-tert-butyl-1H-indole (24 g, 88%). 1H NMR (300 MHz, CDCl3) δ 7.99 (br. s, 1H), 7.54 (d, J=7.2 Hz, 1H), 7.05 (d, J=7.8 Hz, 1H), 7.06-7.13 (m, 2H), 6.26 (s, 1H), 1.39 (s, 9H).

후처리

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

출처 및 근거

ORD 기록
ord-26d036f257a9480e8688165a56ef0c96
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

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