Tetrabutylammonium Fluoride → 4-Chloro-1H-indol-5-ol

HRID 1971410ノート

反応式

HRID 1971410 の反応式
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[C:10]([Cl:16])[C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:16][C:10]1[C:11]([OH:15])=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][NH:6]2

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 674317611-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol

生成物 1

HCID 445500814-Chloro-1H-indol-5-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol (5.35 g, 18.98 mmol) is dissolved in THF (90 mL) and cooled to 0° C. TBAF (4.96 g, 18.98 mmol) is added over 5 minutes to the brown solution. After 1 hour the reaction is quenched with ammonium chloride. The reaction is diluted with ethyl acetate and washed with water and then brine. The organic phase is removed, dried (sodium sulfate) and concentrated. The mixture is absorbed onto silica and purified via FCC (0-40% ethyl acetate:heptanes) to obtain the title compound as a solid. MS (ESI) m/z 168.15 (M+1).

後処理

  1. customAfter 1 hour the reaction is quenched with ammonium chloride
  2. additionThe reaction is diluted with ethyl acetate
  3. washwashed with water
  4. customThe organic phase is removed
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe mixture is absorbed onto silica
  8. custompurified via FCC (0-40% ethyl acetate:heptanes)

出典と根拠

ORDレコード
ord-9cee1dfd93e040408b9fa0b1f5ed617f
出典データセット
uspto-grants-2013_04
特許番号
US08431584B2

反応ノート

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