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

HRID 357311ノート

反応式

HRID 357311 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-3f8ce03d9db94318ac1780661d432f1a
出典データセット
uspto-grants-1998_11
特許番号
US05840738

反応ノート

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