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Methyl 2'-fluoro-5'-(methyloxy)-2-(3,3,5,5-tetramethyl-1-cyclohexen-1-yl)-1,1'-biphenyl-4-carboxylate → Methyl 2'-fluoro-5'-(methyloxy)-2-(3,3,5,5-tetramethylcyclohexyl)-1,1'-biphenyl-4-carboxylate

HRID 1662494
Notes
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Reaction equation

HRID 1662494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[C:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]([CH3:29])([CH3:28])[CH:21]=1>[Pt](=O)=O.CCOC(C)=O.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][C:11]=1[CH:20]1[CH2:25][C:24]([CH3:27])([CH3:26])[CH2:23][C:22]([CH3:29])([CH3:28])[CH2:21]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 57706531Methyl 2'-fluoro-5'-(methyloxy)-2-(3,3,5,5-tetramethyl-1-cyclohexen-1-yl)-1,1'-biphenyl-4-carboxylate

Product 1

HCID 57707074Methyl 2'-fluoro-5'-(methyloxy)-2-(3,3,5,5-tetramethylcyclohexyl)-1,1'-biphenyl-4-carboxylateYield 59.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A screw-cap pressure tube was charged with 69.31B (0.22 g, 0.55 mmol), 1:1 EtOAc/MeOH (10 mL), and platinum(IV) oxide (0.025 g, 0.11 mmol). The tube was purged three times with H2 at 50 psi and sealed, and the contents were stirred overnight. The mixture was diluted with EtOAc, filtered through silica gel (EtOAc), and concentrated. The crude product was purified by silica gel flash chromatography (0-8% EtOAc/hexane) to afford 69.32A (0.13 g, 59% yield) as a colorless oil.

Workup

  1. customThe tube was purged three times with H2 at 50 psi
  2. customsealed
  3. additionThe mixture was diluted with EtOAc
  4. filtrationfiltered through silica gel (EtOAc)
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-8% EtOAc/hexane)

Sources & evidence

ORD record
ord-28a7a0c61e1f474ca8d54c5af823b32b
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030354B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes