HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium borohydride → (5-Benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | Ethyl 5-benzyl-2-(2,5-difluorophenyl)oxazole-4-carboxylate | HCID 67450146 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (5-Benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methanol | HCID 67451532 | 88.8% |
Reaction Steps
To a solution of ethyl 5-benzyl-2-(2,5-difluorophenyl)oxazole-4-carboxylate (590 mg, 1.72 mmol) in THF (8.6 mL) was slowly added LiBH4 (56.2 mg, 2.58 mmol) at room temperature. The reaction mixture was stirred for overnight. After quenched with water, the reaction mixture was extracted with EtOAc. The organic layers was washed with saturated NaHCO3 solution and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by automatic column chromatography (0 to 100% EtOAc in Hexanes) to yield (5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methanol (460 mg, 88%) as a white solid. LC/MS (uplc): MH+ 302.2, 0.92 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08748626B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-12996be1bd354b2580d003c8cd873a87 |
| Source note | uspto-grants-2014_06 |