Potassium Carbonate → Tert-butyl((4-ethynylbenzyl)oxy)dimethylsilane

HRID 2405646

Reaction equation

HRID 2405646 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=O.[Mg+2]>CO>[C:1]([Si:5]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=1)([CH3:21])[CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 59417152Tert-butyldimethyl(4-((trimethylsilyl)ethynyl)benzyloxy)silane

Product 1

HCID 59417173Tert-butyl((4-ethynylbenzyl)oxy)dimethylsilaneYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under argon condition, tert-butyldimethyl((4-((trimethylsilyl)-ethynyl)benzyl)oxy)silane (383 mg, 2.40 mmol) and potassium carbonate (332 mg, 2.40 mmol) were dissolved in 4 mL of methanol, and then stirred for 2 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (5 mL×4) and the organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 280 mg (1.14 mmol, 95%) of the desired compound.

Workup

  1. customUpon completion of the reaction
  2. customthe reaction was terminated
  3. additionby adding 10 mL of aqueous saturated ammonium chloride solution
  4. extractionThe reaction mixture was extracted with ethyl acetate (5 mL×4)
  5. customthe organic layer thus obtained
  6. customto remove water
  7. filtrationThe precipitate was filtered out
  8. concentrationthe resulting solution was concentrated by distillation under reduced pressure
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-1a1fefe3f9d94d0fbe06f38aced62666
Source dataset
uspto-grants-2014_08
Patent number
US08809012B2

Linked notes

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