Aluminium lithium hydride → HCID 22638808, compound

HRID 2416285Notes

Reaction equation

HRID 2416285 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)=O.C(#N)C.CON(C)[C:16]([CH:18]1[CH2:20][CH:19]1[C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[CH:26][NH:27]2)=[CH:23][CH:22]=1)=[O:17]>C1COCC1.CCOCC>[NH:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([CH:19]3[CH2:20][CH:18]3[CH:16]=[O:17])[CH:29]=2)[CH:25]=[CH:26]1

Participants

6

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 86587134Acetonitrile dry iceHCID 86587689HCID 86587689, compound

Product 1

HCID 22638808HCID 22638808, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (30 mg, 7.86 mmol) was suspended in anhydrous THF at −45° C. (dry ice/acetonitrile) with stirring. The 2-(1H-indol-6-yl)-cyclopropanecarboxylic acid methoxy-methyl-amide was dissolved in anhydrous THF and added dropwise over a period of 10 min. The reaction was stirred for 3 h at this temperature, diluted with ether, then quenched with 1.5 mL of 1 N sodium hydroxide solution. The mixture was allowed to warm to room temperature and the resulting white solid was filtered and washed with ether. The ether layer was then concentrated in vacuo to give 2-(1H-indol-6-yl)-cyclopropanecarbaldehyde as a yellow solid. This material was used immediately for the next reaction.

Workup

  1. additionadded dropwise over a period of 10 min
  2. stirringThe reaction was stirred for 3 h at this temperature
  3. customquenched with 1.5 mL of 1 N sodium hydroxide solution
  4. filtrationthe resulting white solid was filtered
  5. washwashed with ether
  6. concentrationThe ether layer was then concentrated in vacuo

Sources & evidence

ORD record
ord-c064a41f0aaf418991da9d9b3bd122df
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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