Aluminium lithium hydride → HCID 21866519, compound

HRID 1582922Notes

Reaction equation

HRID 1582922 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1[C:13]([CH3:14])=[C:12]([C:15](OCC)=[O:16])[S:11][CH:10]=1)#[N:8]>O1CCCC1>[OH:16][CH2:15][C:12]1[S:11][CH:10]=[C:9]([C:7]#[N:8])[C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21866489HCID 21866489, compound

Product 1

HCID 21866519HCID 21866519, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.44 g (64 mmol) of lithium aluminum hydride were added portionwise at 0° C. to a solution of 25.1 g (129 mmol) of ethyl 3-cyano-4-methylthiophene-5-carboxylate in 400 ml of tetrahydrofuran. The mixture was stirred for 5 hours at room temperature, excess reducing agent was destroyed by adding 0.5 N hydrochloric acid, and the reaction mixture was concentrated under a water pump vacuum, diluted with water and extracted three times with ethyl acetate. The combined organic phases were then washed in each case once with 0.5 N hydrochloric acid and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under a water pump vacuum at room temperature. The residue was purified by column chromatography (eluant dichloromethane/methanol 95:5), and 16.1 g (83%) of the desired compound were obtained as a slightly yellow oil.

Workup

  1. customwas destroyed
  2. additionby adding 0.5 N hydrochloric acid
  3. concentrationthe reaction mixture was concentrated under a water pump vacuum
  4. additiondiluted with water
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic phases were then washed in each case once with 0.5 N hydrochloric acid and saturated sodium chloride solution
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationthe desiccant was filtered off
  9. distillationthe solvent was distilled off under a water pump vacuum at room temperature
  10. customThe residue was purified by column chromatography (eluant dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-9bf64785d96c4498b4d083d8514055e8
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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