Tetrabutylammonium Fluoride → 5-Ethynyl-1H-indole

HRID 340253노트

반응식

HRID 340253 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 178425855-Ethynyl-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e541765ed964fadaf928b3a44be6293
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895577B2

반응 노트

불러오는 중…