Aluminium lithium hydride → 3-(4-Fluorophenyl)propanal

HRID 1592350Notes

Reaction equation

HRID 1592350 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](N(OC)C)=[O:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH:10]=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22612404N-Methoxy-N-methyl-4-fluoro-benzenepropanamide

Product 1

HCID 101977823-(4-Fluorophenyl)propanal

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The crude amide was dissolved in ether and cooled in an ice bath and treated with LAH (1.35 g, 35 mmol) and stirred for 1 hour. The reaction was quenched with 1 N HCl, extracted with ethyl acetate and washed successively with water and brine, dried over MgSO4. The extract was filtered and evaporated under vacuum to give 4.3 g of 3-(4-fluorophenyl)propanal.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction was quenched with 1 N HCl
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationThe extract was filtered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-8fc62ebd43a44bc299c210eec26b1a11
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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