Tetrabutylammonium Fluoride → 5-Ethynyl-1H-indole

HRID 1479539ノート

反応式

HRID 1479539 の反応式
C([Si]([C:8]#[C:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:9]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)#[CH:8]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 668932335-[(Triethylsilyl)ethynyl]-1H-indole

生成物 1

HCID 178425855-Ethynyl-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-((triethylsilyl)ethynyl)-1H-indole (from the previous step) in THF (0.2 M) cooled at 0° C. was treated with a solution (0.5 eq.) of tetrabutylammonium fluoride in a dropwise fashion. The reaction mixture turned black and was continued to stir for 30 minutes before warming up to rt. TLC showed full conversion. The reaction was quenched with water and was extracted with diethylether. Combined organic layers were dried over anhydrous Na2SO4 and concentrated using rotary evaporator with minim heating. Chromatography (silica gel, diethylether) afforded the product 5-ethynyl-1H-indole as colorless oil.

後処理

  1. customThe reaction was quenched with water
  2. extractionwas extracted with diethylether
  3. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customevaporator with minim
  6. temperatureheating

出典と根拠

ORDレコード
ord-93d6a7be45534d8cb1af09e3e853755e
出典データセット
uspto-grants-2016_08
特許番号
US09408907B2

反応ノート

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