(2-Cyclopropyl-4'-fluoro-5-isopropoxybiphenyl-4-yl)methanol → 2-Cyclopropyl-4'-fluoro-5-isopropoxybiphenyl-4-carbaldehyde

HRID 531003Notes

Reaction equation

[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:1]1([C:4]2[CH:9]=[C:8]([CH:10]=[O:11])[C:7]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:6][C:5]=2[C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

Manganese dioxide (16.6 g) was added to a toluene (80 mL) solution of (2-cyclopropyl-4′-fluoro-5-isopropoxybiphenyl-4-yl)methanol (5.75 g), and the mixture was stirred at 60° C. for 1 hour in a nitrogen atmosphere. The reaction mixture was filtered, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (4.54 g).

Workup

filtrationThe reaction mixture was filtered
distillationthe solvent was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-70c10c545b9d46c1b634ecd50de5faa9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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