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

HRID 2084817Notes

Reaction equation

HRID 2084817 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-5aa010a527b04073ac73dff28f5bb7a3
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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