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1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole → 1-(3-Hydroxybenzyl)-5-methoxy-2-phenylindole

HRID 1191651
ノート
印刷プレビュー

反応式

HRID 1191651 の反応式
C([O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.O.CSC>[OH:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 696710521-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole

生成物 1

HCID 696709171-(3-Hydroxybenzyl)-5-methoxy-2-phenylindole収率 70%

試薬・触媒・溶媒 1

HCID 86597598Trifluoroacetic acid water dimethylsulfide溶媒

実験手順

1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole (200 mg) was dissolved in trifluoroacetic acid-water-dimethyl sulfide (95/5/10, 4.8 mL), and the solution was stirred at room temperature for 68 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (110 mg).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-017956df7c7b4e1596a409f3717b2702
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680120B2

反応ノート

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