Tetrabutylammonium Fluoride → 2-Phenyl-1H-indol-4-ol

HRID 1585795ノート

反応式

HRID 1585795 の反応式
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:13]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:13]2

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 211830744-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-phenyl-1H-indole

生成物 1

HCID 167416562-Phenyl-1H-indol-4-ol収率 84.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-t-Butyldimethylsilyoxy-2-phenylindole (55 mg, 0.17 mmol) was dissolved in THF (10 ml) at 0° C. and treated with tetrabutylammonium flouride (0.5 ml, 1.0M in THF, excess). After stirring at this temperature for 10 minutes, the reaction was quenched by addition of saturated ammonium chloride. The mixture was extracted several time with ethyl acetate, dried over magnesium sulfate, and evaporated to give a crude oil. Flash chromatography (5% ethyl acetate/hexanes) provided the desired phenol (30 mg, 84.8%) as a white solid. NMR. MS.

後処理

  1. customthe reaction was quenched by addition of saturated ammonium chloride
  2. extractionThe mixture was extracted several time with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a crude oil

出典と根拠

ORDレコード
ord-4c507bc631b54ca78ffb47dca589602a
出典データセット
uspto-grants-1999_08
特許番号
US05939443

反応ノート

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