Water → 3,5-Dimethyl-1-benzofuran-2-carbaldehyde

HRID 2091125Notes

Reaction equation

HRID 2091125 reaction equation
CON(C)[C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:9]=2[C:10]=1[CH3:11])=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:11][C:10]1[C:9]2[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:8]=2[O:7][C:6]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86662731N-methoxy-N,3,5-trimethyl-1-benzofuran-2-carboxamide

Product 1

HCID 31596873,5-Dimethyl-1-benzofuran-2-carbaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (50 mL) of N-methoxy-N,3,5-trimethyl-1-benzofuran-2-carboxamide (3.78 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (307 mg) at −78° C., and the mixture was stirred for 2 hr. Water (350 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (700 μL) was added, and the mixture was stirred at room temperature for 1 hr. The resulting insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with hexane to give the title object compound (2.08 g, 74%) as a yellow solid.

Workup

  1. customto quench
  2. customthe reaction, 1N aqueous sodium hydroxide solution (700 μL)
  3. additionwas added
  4. stirringthe mixture was stirred at room temperature for 1 hr
  5. filtrationThe resulting insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-b6383a2e2396445885fc0ac1aade4f05
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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