HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dibromoethane → HCID 86680887, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dibromoethane | HCID 7839 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)acetonitrile | HCID 67287289 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86680887 | HCID 86680887 | 72.2% |
Reaction Steps
To a solution of β-39 (4.0 g, 5.93 mmol) in toluene (40 mL) were added 1,2-dibromethane (0.8 mL, 8.90 mmol), tetrabutylammonium bromide (0.4 g, 1.19 mmol) and aq. 50% NaOH solution (40 mL). The mixture was stirred at room temperature for 15 h. After dilution with water, the mixture was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 42 (3.0 g, 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08586550B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-5e7dec49db8540e29acc60c8ff4b52f8 |
| Source note | uspto-grants-2013_11 |