HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Tricyclohexylphosphine | HCID 75806 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | Methyl(4-(((trifluoromethyl)sulfonyl)oxy)-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate | HCID 131734520 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate | HCID 131734522 | 91.4% |
Reaction Steps
To a mixture of methyl(4-(((trifluoromethyl)sulfonyl)oxy)-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (512 mg) and DMF (10 mL) were added cyclopropylboronic acid (167 mg), potassium phosphate (1238 mg), Pd(OAc)2 (21.83 mg) and tricyclohexylphosphine (82 mg) at room temperature, and the mixture was refluxed for 16 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (372 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09238639B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-7dff6fd2eecb4fe98a755433b3f20f07 |
| Source note | uspto-grants-2016_01 |