Hydrochloric Acid → 7-Methoxy-1-benzofuran-2-carbaldehyde

HRID 1057934Notes

Reaction equation

HRID 1057934 reaction equation
[C:1]([C:3]1[O:4][C:5]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)#N.CC(C[AlH]CC(C)C)C.C[OH:24].Cl>ClCCl.C1(C)C=CC=CC=1>[CH3:13][O:12][C:11]1[C:5]2[O:4][C:3]([CH:1]=[O:24])=[CH:7][C:6]=2[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 2985567-Methoxybenzofuran-2-carbonitrile

Product 1

HCID 34573107-Methoxy-1-benzofuran-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

2-Cyano-7-methoxybenzofuran (0.736 g) was dissolved in dichloromethane (10 ml), and a 1.02N DIBAL solution (5.4 ml) in toluene was added thereto at −4 to −30° C., followed by stirring for one hour. Methanol and dilute hydrochloric acid were added to the mixture, and the solvent was distilled off. The obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1) to give Compound IIad-a (0.371 g, 50%) as an oily substance.

Workup

  1. customat −4 to −30° C.
  2. distillationthe solvent was distilled off
  3. customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1)
  4. customto give Compound IIad-a (0.371 g, 50%) as an oily substance

Sources & evidence

ORD record
ord-9e9b1694743a4449b93ddf0f1ade65b4
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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