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

HRID 1716780Notes

Reaction equation

HRID 1716780 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6ae4dd0783a249d29bdd995a0fd001f6
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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