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

HRID 268898노트

반응식

HRID 268898 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-17fb9d1c4666491792b2671de2fd4c1d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446118B2

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