HCID 57870269, compound → HCID 57501693, compound

HRID 2384861Notes

Reaction equation

HRID 2384861 reaction equation
[CH:1]([Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[O:15][CH3:16])([CH3:3])[CH3:2].[H][H]>CCO.[Pd]>[CH3:16][O:15][C:7]1[CH:8]=[C:9]([NH2:12])[CH:10]=[CH:11][C:6]=1[O:5][Si:4]([CH:17]([CH3:19])[CH3:18])([CH:20]([CH3:22])[CH3:21])[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 57870269HCID 57870269, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57501693HCID 57501693, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve triisopropyl-(2-methoxy-4-nitro-phenoxy)-silane (95.7 g, 294.0 mmol) in EtOH (1800 mL) and add 5% Pd/C (10.0 g). Hydrogenate the slurry at RT under 50 psi hydrogen for 8 h. Filter the slurry through a pad of Celite® and rinse with EtOH. Concentrate the filtrate in vacuo to give a brown oil. Purify the oil by flash chromatography, using a gradient from 100% hexanes to 20% EtOAc/hexanes, to provide 67.4 g (77.6%) of the title compound as a brown solid. MS/ES m/z 296.2 [M+H]+.

Workup

  1. filtrationFilter the slurry through a pad of Celite®
  2. washrinse with EtOH
  3. concentrationConcentrate the filtrate in vacuo
  4. customto give a brown oil
  5. customPurify the oil by flash chromatography

Sources & evidence

ORD record
ord-fd99d8e05d6546f88e80975f3eab0fea
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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