Aluminium lithium hydride → HCID 67550417, compound

HRID 1836636Notes

Reaction equation

HRID 1836636 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]-cyclopropanecarboxylic acid ethyl ester (1.0 g) as an amber oil. LC-MS: 1.49 min; 291.1 (MNa)+.

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-d93280d44f18483393f462b4b6db9fc9
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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