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

HRID 468391

反応式

HRID 468391 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 5941662-tert-Butyl-1H-indole収率 88%

試薬・触媒・溶媒 1

HCID 178418339Butyllithium溶媒

反応条件

温度
15 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-26d036f257a9480e8688165a56ef0c96
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

関連ノート

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