Trimethylsilylacetylene → HCID 14572730, compound

HRID 1916516Notes

Reaction equation

HRID 1916516 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[C:16]([Si:18]([CH3:21])([CH3:20])[CH3:19])#[CH:17]>N1CCCCC1.[Cu]I>[CH2:10]([N:9]([CH2:12][CH3:13])[CH2:8][CH2:7][O:6][C:5]1[CH:14]=[CH:15][C:2]([C:17]#[C:16][Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:3][CH:4]=1)[CH3:11]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 4239532-(4-bromophenoxy)-N,N-diethylethanamine

Product 1

HCID 14572730HCID 14572730, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere a mixture of 5.44 g (20 mmol) [2-(4-bromo-phenoxy)-ethyl]-diethyl-amine, 3.11 mL (22 mmol) ethynyl-trimethyl-silane, 462 mg (0.4 mmol) tetrakis-triphenylphosphane-palladium, 76 mg (0.4 mmol) CuI in 50 mL piperidine is heated to 70° C. for 21 h. 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-b09d235c50064f6bb881e543d8f60808
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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