HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 89442788, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (2-Bromoethoxy)-tert-butyldimethylsilane | HCID 3608067 | — |
| Reactant | HCID 86729312 | HCID 86729312 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 89442788 | HCID 89442788 | 78.8% |
Reaction Steps
To a solution of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (300 mg, 0.593 mmol) in dry DMF (6 mL), was added (2-bromoethoxy)(tert-butyl)dimethylsilane (423 mg, 1.78 mmol) and cesium carbonate (578 mg, 1.78 mmol). The reaction mixture was stirred at r.t. for 36 h. After completion of reaction, as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and washed with water (3×10 mL). The organic layer was dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 2:8 Ethyl acetate:Pet. Ether) to afford title compound (310 mg, 78.8%) as white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09018249B2 |
| Source dataset | uspto-grants-2015_04 |
| ORD ID | ord-a0d813314fec49d884b3b331359c7c86 |
| Source note | uspto-grants-2015_04 |