Aluminium lithium hydride → HCID 67550417, compound

HRID 2416259Notes

Reaction equation

HRID 2416259 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]([CH:12]1[CH2:14][CH:13]1[C:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[C:26]#[N:27])=[O:16])=[O:11])[CH3:8]>O1CCCC1>[CH2:7]([O:9][C:10]([CH:12]1[CH2:14][CH:13]1[CH:15]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[C:26]#[N:27])[OH:16])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69846066HCID 69846066, compound

Product 1

HCID 67550417HCID 67550417, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

A suspension of lithium aluminum hydride (0.3 g, 7.94 mmol) in anhydrous tetrahydrofuran (50 ml) was cooled to −45° C. and treated with a solution of the 2-(3-Cyano-1H-indole-5-carbonyl)-cyclopropanecarboxylic acid ethyl ester (1.12 g dissolved in 10 ml THF). The mixture was stirred for 1 h and quenched with water followed by sodium hydroxide solution. The aluminum salts were removed by filtration. The filtrate was concentrated in vacuo to afford 2-[(3-cyano-1H-indol-5-yl)-hydroxy-methyl]-cyclopropanecarboxlic acid ethyl ester (1.0 g) as an amber oil.

Workup

  1. customquenched with water
  2. customThe aluminum salts were removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3f074f160d2c4c9782e8992c89cfdd11
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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