Hydrochloric Acid → 7-Methoxy-1-benzofuran-2-carbaldehyde
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]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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
- customat −4 to −30° C.
- distillationthe solvent was distilled off
- customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=10/1)
- 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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