Trimethylsilylacetylene → (3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilane

HRID 1927242Notes

Reaction equation

HRID 1927242 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Mg]Br)C.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].N>[Cu]Br.C1COCC1>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:25][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 66111TrimethylsilylacetyleneHCID 700424-Benzyloxybenzyl chlorideHCID 20976574Ammonia chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 42642731(3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilane

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of THF (20 mL) and trimethylsilylacetylene (850 μL) was added ethyl magnesium bromide (3M diethyl ether solution, 1.9 mL) at room temperature under a nitrogen atmosphere, which was stirred for 40 minutes at 65° C. The reaction solution was cooled to room temperature, after which copper(I) bromide (310 mg) and 4-benzyloxybenzyl chloride (81.0 g) were added to the reaction solution, which was stirred for 8 hours and 45 minutes at 65° C. A saturated aqueous ammonia chloride solution was added at room temperature to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the titled compound (910 mg).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringwas stirred for 8 hours and 45 minutes at 65° C
  3. extractionwas then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-242afa1f23144ff2ac037d5ca185fb25
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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