1-(2,6-Dimethyl-4-triisopropylsilanyloxyphenyl)-1-(4'-fluoro-3'-isopropenylphenyl)methanol → 3,5-Dimethyl-4-(4'-fluoro-3'-iso-propylbenzyl)triisopropylsilanoxybenzene

HRID 2108622Notes

Reaction equation

HRID 2108622 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH:5]=[C:4]([CH3:19])[C:3]=1[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([C:29]([CH3:31])=[CH2:30])[CH:23]=1)O>CCO.CC(O)=O.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][Si:9]([CH:10]([CH3:12])[CH3:11])([CH:13]([CH3:15])[CH3:14])[CH:16]([CH3:18])[CH3:17])[CH:5]=[C:4]([CH3:19])[C:3]=1[CH2:20][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[C:24]([CH:29]([CH3:31])[CH3:30])[CH:23]=1

Participants

4

Reactant 1

HCID 666427661-(2,6-Dimethyl-4-triisopropylsilanyloxyphenyl)-1-(4'-fluoro-3'-isopropenylphenyl)methanol

Product 1

HCID 666430853,5-Dimethyl-4-(4'-fluoro-3'-iso-propylbenzyl)triisopropylsilanoxybenzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of 1-(2,6-dimethyl-4-triisopropylsilanyloxyphenyl)-1-(4′-fluoro-3′-isopropenylphenyl)methanol (1.2 g, 2.71 mmol) and Pd/C (0.1 g, 10%) in EtOH/HOAc (9:1, 10 mL) was stirred under a H2 atmosphere for 16 h. The reaction mixture was filtrated through a plug of Celite and concentrated to afford the crude 3,5-dimethyl-4-(4′-fluoro-3′-iso-propylbenzyl)triisopropylsilanoxybenzene that was used for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtrated through a plug of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fef4f6412573411d8cc5193e9c6c18d1
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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