Aluminium lithium hydride → HCID 89924462, compound

HRID 1500933Notes

Reaction equation

HRID 1500933 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:12]([C:24](OCC)=[O:25])=[CH:11]2>C1COCC1>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:12]([CH2:24][OH:25])=[CH:11]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 89924249HCID 89924249, compound

Product 1

HCID 89924462HCID 89924462, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of LiAlH4 (0.38 g, 10.0 mmol) in 50 mL of THF was added a solution of ethyl 5-chloro-1-[3-(methylsulfonyl)propyl]-1H-indole-2-carboxylate (1.60 g, 4.6 mmol) dropwise at 0° C. The reaction mixture was warmed naturally to RT and then stirred at RT for 2 hours. The reaction was then quenched with methanol. The resulting mixture was filtered through a celite pad. The filtrate was concentrated in vacuo to afford the crude [5-chloro-1-(3-methanesulfonyl-propyl)-1H-indol-2-yl]-methanol (0.60 g, yield: 43.3%).

Workup

  1. customThe reaction was then quenched with methanol
  2. filtrationThe resulting mixture was filtered through a celite pad
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-075a71acf8ab471e827bcec9ac322f35
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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