(4-Phenylfuran-3-yl)methanol → 4-Phenyl-3-furaldehyde

HRID 915672

Reaction equation

[C:1]1([C:7]2[C:8]([CH2:12][OH:13])=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]1([C:7]2[C:8]([CH:12]=[O:13])=[CH:9][O:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Prepare a solution of (4-phenylfuran-3-yl)methanol (2.3 g, 13.2 mmol) in methylene chloride (20 mL). Add N-methylmorpoline N-oxide (2.2 g, 18.5 mmol) and powdered 4 Å molecular sieves. Cool the mixture to 0° C. and add tetra-n-propyl ammonium perruthenate. Warm the mixture to room temperature and stir for an additional 3 hours. Filter the reaction mixture through Celite® and concentrate the filtrate. Perform flash chromatography on silica gel eluting with 10% diethyl ether/hexane to afford 1.36 g of 4-phenyl-3-formylfuran. 1H NMR (CDCl3) δ 10.01 (s, 1H), 8.15 (s, 1H), 7.60 (s, 1H), 7.35-7.54 (m, 5H).

Workup

temperatureWarm the mixture to room temperature
filtrationFilter the reaction mixture through Celite®
concentrationconcentrate the filtrate

Sources & evidence

ORD record: ord-d01dd0173fa64666a2494a297d85a9a0
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265246B2

Linked notes

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