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
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- customThe tube was purged three times with H2 at 50 psi
- customsealed
- additionThe mixture was diluted with EtOAc
- filtrationfiltered through silica gel (EtOAc)
- concentrationconcentrated
- 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
- Patent number
- US08030354B2
Reaction notes
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