2-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1-ethenyl-4-methoxybenzene → HCID 22662105, compound

HRID 392877Notes

Reaction equation

HRID 392877 reaction equation
[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH:16]=[CH2:17])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C>[C:1]([Si:5]([CH3:19])([CH3:18])[O:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][CH3:17])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 226620962-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1-ethenyl-4-methoxybenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22662105HCID 22662105, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

25.0 g (0.0899 mol) of tert-butyl-dimethyl-(2-vinyl-5-methoxy-benzyloxy)-silane (15) was dissolved in 100 mL of ethyl acetate and was placed in a 1 L Parr Shaker bottle. 1.93 g (0.0084 mol) of catalyst (PtO2) was added and the solution was placed under 30 PSI of hydrogen for 25 minutes. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to yield crude product. The crude product was chromatographed on a silica gel column with 40% CHCl3 in hexane to afford 24.85 g (99%) of tert-butyl-dimethyl-(2-ethyl-5-methoxy-benzyloxy)-silane (16).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customto yield crude product
  4. customThe crude product was chromatographed on a silica gel column with 40% CHCl3 in hexane

Sources & evidence

ORD record
ord-6618c2e733d449348a4a9d0a43b884b0
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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