Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]- → HCID 21898100, compound

HRID 1374955Notes

Reaction equation

HRID 1374955 reaction equation
[CH2:1]([Li])CCC.[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH3:19])=[CH:14][CH:13]=1)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:6]([Si:10]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:1])=[CH2:19])=[CH:14][CH:13]=1)([CH3:22])[CH3:21])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 10857908Ethanone, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-HCID 178418339Butyllithium

Product 1

HCID 21898100HCID 21898100, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl(triphenylphosphonium) bromide (17.1 g, 48.0 mmol) was suspended in THF (96 mL) and cooled to 0° C. n-Butyllithium (2.5 M in hexane, 19.2 mL, 48.0 mmol) was added dropwise to the mixture. The red solution was stirred at rt for 0.5 h. 1-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-ethanone (10.0 g, 40.0 mmol) was added. The solution turned bright yellow and a white precipitate formed. The mixture was stirred for 1 h at rt and then the solution was quenched with saturated NaHCO3. The aqueous phase was extracted with diethyl ether and the combined organic layers were washed with saturated NaHCO3. The organic layers were dried over sodium sulfate, filtered and concentrated. The resultant mixture was eluted through a plug of silica gel (hexanes) and the filtrate was concentrated to provide tert-butyl-(4-isopropenyl-phenoxy)-dimethyl-silane (8.36 g, 84%) as a colorless oil. ESI MS (m/z 249, M+H).

Workup

  1. additionwas added dropwise to the mixture
  2. customa white precipitate formed
  3. stirringThe mixture was stirred for 1 h at rt
  4. customthe solution was quenched with saturated NaHCO3
  5. extractionThe aqueous phase was extracted with diethyl ether
  6. washthe combined organic layers were washed with saturated NaHCO3
  7. dry with materialThe organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe resultant mixture was eluted through a plug of silica gel (hexanes)
  11. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c9c7fe2206f149bbba131367c66312d9
Source dataset
uspto-grants-2007_01
Patent number
US07166628B2

Reaction notes

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