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

HRID 640139Notes

Reaction equation

HRID 640139 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-].[NH4+]>O1CCCC1.[Cu]Br>[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 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 700424-Benzyloxybenzyl chlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 42642731(3-(4-Benzyloxy-phenyl)-prop-1-ynyl)-trimethylsilaneYield 72%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of trimethylsilyl acetylene (851 μL, 6.02 mmol) in tetrahydrofuran (20 mL) was added ethyl magnesium bromide (3 M diethyl ether solution, 1.86 mL, 5.59 mmol) under nitrogen atmosphere at room temperature, which was stirred for 40 minutes at 65° C. The reaction solution was cooled to room temperature, and copper (I) bromide (308 mg, 2.16 mmol) and 4-benzyloxybenzyl chloride (1.00 g, 4.30 mmol) were added to the reaction solution and stirred for 8 hours and 45 minutes at 65° C. Saturated ammonium chloride solution was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and 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 title compound (911 mg, 72%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. stirringstirred for 8 hours and 45 minutes at 65° C
  3. extractionwhich was then extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  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-46368d12b5954a48bd195e6185678ca7
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

Loading…