{2-Ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol → 2-Ethyl-5-[4-(trifluoromethyl)phenyl]-3-furaldehyde

HRID 1876938

Reaction equation

[CH2:1]([C:3]1[O:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH2:8][OH:9])[CH3:2]>C(OCC)C.O1CCCC1.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[O:4][C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:11]=2)=[CH:6][C:7]=1[CH:8]=[O:9])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of {2-ethyl-5-[4-(trifluoromethyl)phenyl]-3-furyl}methanol (2.7 g) and manganese dioxide (6.8 g) in diethyl ether (20 mL) and tetrahydrofuran (20 mL) was stirred overnight at 40° C. Manganese dioxide was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (5% ethyl acetate/hexane to 20% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (0.66 g, 24%) as a yellow solid.

Workup

filtrationManganese dioxide was filtered off
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel chromatography (5% ethyl acetate/hexane to 20% ethyl acetate/hexane)
customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record: ord-702d166f9b8142d3b86b750a9e79e101
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Linked notes

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