Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | HCID 57849346 | HCID 57849346 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57849320 | HCID 57849320 | 81.2% |
Reaction Steps
4-[1-Ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-2-methyl-benzoic acid methyl ester (11.20 g, 24.43 mmol) in DMF (100 ml) is added trimethylsilylacetylene (6.90 ml, 48.85 mmol), dichlorobis(triphenylphosphine) palladium (1.71 g, 2.44 mmol) and triethylamine (23.84 ml, 171 mmol) and heated to 80° C. overnight. The reaction mixture is concentrated and filtered through a pad of silica gel eluted with 10% EtOAc/Hexanes. The eluent is concentrated and chromatographed (330 g SiO2, 2% EtOAc/Hexanes) to yield the title compound (8.07 g, 81%) as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07595345B2 |
|---|
| Source dataset | uspto-grants-2009_09 |
|---|
| ORD ID | ord-ae1c3d909cba4c55a317f18212f2faac |
|---|
| Source note | uspto-grants-2009_09 |
|---|