(2-Cyclopropyl-5-ethoxy-4'-fluorobiphenyl-4-yl)methanol → 2-Cyclopropyl-5-ethoxy-4'-fluorobiphenyl-4-carbaldehyde

HRID 530986Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Manganese dioxide (17.2 g) was added to a toluene (30 mL) solution of (2-cyclopropyl-5-ethoxy-4′-fluorobiphenyl-4-yl)methanol (5.65 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 (4.66 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-1f318e558794485aab5bd71a6373a0bd
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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