Tetrabutylammonium Fluoride → 5-Ethynyl-1H-indole

HRID 1259121ノート

反応式

HRID 1259121 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 minimum 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 minimum heating

出典と根拠

ORDレコード
ord-5158d4b5471b480dbb21c6b308620778
出典データセット
uspto-grants-2013_06
特許番号
US08466167B2

反応ノート

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