HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → HCID 22049033, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Carbamic acid, [2-(3,4-difluorophenyl)-1-(hydroxymethyl)ethyl]-, 1,1-dimethylethyl ester | HCID 22048830 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 22049033 | HCID 22049033 | 76% |
Reaction Steps
To a well stirred suspension of 95% NaH (0.12 g, 5.0 mmol) in THF (20 mL) at r.t. was added a solution of (+)-[1-(3,4-difluorobenzyl)-2-hydroxy-ethyl]-carbamic acid-tert-butyl ester (1.0 g; 4.0 mmol) in 10 mL THF via a dropping funnel at room temperature. The resulting suspension was stirred for 3 h and then quenched carefully with 10 mL of water. The biphasic mixture was extracted with 50 mL of Et2O, washed with brine, filtered and the solvent was removed in vacuo. The gummy residue thus obtained was purified by column chromatography over silica gel (Rf =0.25, 3:2 hexane-EtOAc) to obtain (+)-4-(3,4-difluoro-benzyl)-oxazolidin-2-one as a white solid (0.32 g, 76%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06159990 |
| Source dataset | uspto-grants-2000_12 |
| ORD ID | ord-4027649398e34d1498696a41a942f428 |
| Source note | uspto-grants-2000_12 |