Aluminium lithium hydride → 2-(1-benzenesulfonyl-1H-indol-5-yl)-2-phenyl-ethanol

HRID 268898ノート

反応式

HRID 268898 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(=O)C[CH:11]([C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH:22]=[CH:21]2)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:37][O:38]C(=O)C=CC1C=C2C(=CC=1)N(S(C1C=CC=CC=1)(=O)=O)C=C2>O1CCCC1>[C:30]1([S:27]([N:23]2[C:24]3[C:20](=[CH:19][C:18]([CH:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:37][OH:38])=[CH:26][CH:25]=3)[CH:21]=[CH:22]2)(=[O:29])=[O:28])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

5

反応物 3

HCID 21226445Aluminium lithium hydrideHCID 598319063-(1-benzenesulfonyl-1H-indol-5-yl)-3-phenyl-propionic acid methyl esterHCID 673571463-(1-benzenesulfonyl-1H-indol-5-yl)-acrylic acid methyl ester

生成物 1

HCID 598316292-(1-benzenesulfonyl-1H-indol-5-yl)-2-phenyl-ethanol収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of lithium aluminum hydride (1.0 M in THF, 5.9 mL) was added dropwise to a solution of the above obtained mixture 10/1: 3-(1-benzenesulfonyl-1H-indol-5-yl)-3-phenyl-propionic acid methyl ester and 3-(1-benzenesulfonyl-1H-indol-5-yl)-acrylic acid methyl ester CCLXVI (1.654 g, 3.935 mmol) in tetrahydrofuran (30 mL) at 0° C. After stirring for 1 hour the reaction was quenched by slow addition, at 0° C., of Rochelle salt and water. The resulting mixture was diluted with ethyl acetate and stirred at room temperature overnight. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography to afford 1.06 g (69% yield) of 2-(1-benzenesulfonyl-1H-indol-5-yl)-2-phenyl-ethanol CCLXVII.

後処理

  1. customat 0° C
  2. customwas quenched by slow addition, at 0° C., of Rochelle salt and water
  3. additionThe resulting mixture was diluted with ethyl acetate
  4. stirringstirred at room temperature overnight
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-17fb9d1c4666491792b2671de2fd4c1d
出典データセット
uspto-grants-2008_11
特許番号
US07446118B2

反応ノート

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