Water → 6-Fluoro-3-methyl-1-benzofuran-2-carbaldehyde

HRID 2091144Notes

Reaction equation

HRID 2091144 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]([CH3:15])=[C:7]([C:9](N(OC)C)=[O:10])[O:8][C:4]=2[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]([CH3:15])=[C:7]([CH:9]=[O:10])[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 866627326-fluoro-N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide

Product 1

HCID 823743336-Fluoro-3-methyl-1-benzofuran-2-carbaldehydeYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (50 mL) of 6-fluoro-N-methoxy-N,3-dimethyl-1-benzofuran-2-carboxamide (3.65 g) synthesized above in tetrahydrofuran was added lithium aluminum hydride (292 mg) at 0° C., and the mixture was stirred for 1 hr. Water (300 μL) was added to quench the reaction, 1N aqueous sodium hydroxide solution (600 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 purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (1.88 g, 69%) as a pale-yellow solid.

Workup

  1. customto quench
  2. customthe reaction, 1N aqueous sodium hydroxide solution (600 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. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-69855ed9f1ba4739a676046e025a6b62
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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