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

HRID 531121Notes

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][CH:18]=[CH:17][C:16]=2[F:21])[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:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

Manganese dioxide (1.61 g) was added to a toluene (10 mL) solution of (2-cyclopropyl-5-ethoxy-2′-fluorobiphenyl-4-yl)methanol (1.06 g), and the mixture was stirred at 60° C. for 1 hour. Manganese dioxide (0.965 g) was further added to the reaction mixture, and the mixture was stirred at 60° C. for 30 minutes. 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 (955 mg).

Workup

stirringthe mixture was stirred at 60° C. for 30 minutes
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-003279b0d5e54a70a9ac6dc74ebb923d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353108B2

Reaction notes

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