(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane → HCID 69253921, compound

HRID 902621Notes

Reaction equation

HRID 902621 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](I)[CH:6]=1.[Si:13]([O:20][CH2:21][CH2:22][C:23]#[CH:24])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CCN(CC)CC.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:24]#[C:23][CH2:22][CH2:21][O:20][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:6]=1

Participants

6

Reactant 2

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneHCID 21939462Methyl 2-(3-iodophenyl)acetate

Product 1

HCID 69253921HCID 69253921, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of (3-iodo-phenyl)-acetic acid methyl ester (948 mg, 3.4 mmol), 1-(t-butyldimethylsilyloxy)but-3-yne (644 mg, 3.5 mmol), copper(1)iodide (50 mg), and bis(triphenylphosphine)-palladium(II)chloride (50 mg) in Et3N (5 ml) was refluxed, under argon for 2 hr. The reaction was cooled, and the liquid was decanted off, diluted with diethyl ether, and washed with 1N HCl. The organic layer was dried and the solvent was evaporated. The residue was chromatographed on silica gel (hexane/methylene chloride 60/40) to give the title compound as an oil (700 mg, 62%). MS (ESI) 333.0 (M+H)+.

Workup

  1. temperaturewas refluxed, under argon for 2 hr
  2. temperatureThe reaction was cooled
  3. customthe liquid was decanted off
  4. additiondiluted with diethyl ether
  5. washwashed with 1N HCl
  6. customThe organic layer was dried
  7. customthe solvent was evaporated
  8. customThe residue was chromatographed on silica gel (hexane/methylene chloride 60/40)

Sources & evidence

ORD record
ord-3b9ec973a43c4d7c873d8715a5a60fa2
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

Loading…