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

HRID 531003
Notes
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Reaction equation

HRID 531003 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 117992161(2-Cyclopropyl-4'-fluoro-5-isopropoxybiphenyl-4-yl)methanol

Product 1

HCID 904237002-Cyclopropyl-4'-fluoro-5-isopropoxybiphenyl-4-carbaldehydeYield 79.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

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

  1. filtrationThe reaction mixture was filtered
  2. distillationthe solvent was distilled off under reduced pressure
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes