HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 57847746, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Bromopinacolone | HCID 21642 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | HCID 20743446 | HCID 20743446 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57847746 | HCID 57847746 | 87.2% |
Reaction Steps
To a solution of 2-(2-fluoropyridin-4-yl)-1-phenylethanone (450 mg, 2.1 mmol) in dry THF (10 mL) at 0° C. was added a solution of sodium bis(trimethylsilyl)amide (2.1 mL, 1M). After 10 min. 1-bromopinacolone (309 μL, 2.3 mmol) was added dropwise and the solution stirred for 2 h. The solution was poured into ethyl acetate (25 mL) and H2O (25 mL) and the layers allowed to separate. The organic layer was collected and the aqueous layer extracted with ethyl acetate (30 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4) and concentrated. The product was purified by flash chromatography using EtOAc-Pet. spirit (20:80) as eluant to give the pure product as a pale yellow oil (574 mg, 87%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07593820B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-fe84fde5652b4341a8cff577e792bc1e |
| Source note | uspto-grants-2009_09 |