Trimethylsilylacetylene → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

HRID 1916521Notes

Reaction equation

HRID 1916521 reaction equation
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].I[C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1>N1CCCCC1.[Cu]I>[CH3:4][Si:3]([C:1]#[C:2][C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidine

Product 1

HCID 673634551-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8082PiperidineSolvent

Procedure

Under a nitrogen atmosphere 7.0 mL (49.5 mmol) ethynyl-trimethyl-silane is slowly added to a mixture of 14.3 g (45 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine, 1.04 g (0.9 mmol) tetrakis-triphenylphosphane-palladium and 171 mg (0.4 mmol) CuI in 140 mL piperidine (exothermic reaction) and stirred for 30 minutes. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

Workup

  1. distillationThe solvent is distilled off i.vac
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-f8d4ea79d767455ca8110c0dc05435f5
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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