Benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol → Benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanone

HRID 2377144Notes

Reaction equation

HRID 2377144 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH2:21][CH3:22])[CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1>C(Cl)Cl.O=[Mn]=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH2:21][CH3:22])[CH:13]=3)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 68936547Benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol

Product 1

HCID 68941709Benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanol (2.36 g crude, 6.8 mmol) in CH2Cl2 (15 mL) at room temperature was added activated MnO2 powder (6.0 g, 69 mmol) and kept adding 2˜3 equivalents of MnO2 every 3˜5 h until HPLC showed disappearance of the starting material. The black suspension was filtered through a Celite pad, concentrated in vacuo to give benzofuran-5-yl-(3-ethoxy-4-methoxy-phenyl)-methanone as an off-white solid (2.25 g, 111% crude yield). The product was used in the next step without further purification.

Workup

  1. filtrationThe black suspension was filtered through a Celite pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c59415a9ac684e10a8ce4478d7665065
Source dataset
uspto-grants-2008_12
Patent number
US07468446B2

Reaction notes

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