Sodium hydride → HCID 22993461, compound

HRID 1167696Notes

Reaction equation

HRID 1167696 reaction equation
[H-].[Na+].C([O:7][C:8](=[O:21])[NH:9][CH2:10][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=1)O)(C)(C)C>C1COCC1>[F:20][C:15]1[CH:14]=[C:13]([CH:11]2[O:21][C:8](=[O:7])[NH:9][CH2:10]2)[CH:18]=[CH:17][C:16]=1[F:19]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22993583HCID 22993583, compound

Product 1

HCID 22993461HCID 22993461, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a well stirred suspension of 95% NaH (0.55 g, 11.8 mmol) in THF (20 mL) at room temperature was added a solution of [2-(3,4-difluorophenyl)-2-hydroxy-ethyl]-carbamic acid-tert-butyl ester (3.2 g, 23.0 mmol) in 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 100 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=0.15, 3:2 hexane-EtOAc) to obtain 5-(3,4-difluoro-phenyl)-oxazolidin-2-one as a white solid (1.1 g, 47%).

Workup

  1. stirringThe resulting suspension was stirred for 3 h
  2. customquenched carefully with 10 mL of water
  3. extractionThe biphasic mixture was extracted with 100 mL of Et2O
  4. washwashed with brine
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe gummy residue thus obtained
  8. customwas purified by column chromatography over silica gel (Rf=0.15, 3:2 hexane-EtOAc)

Sources & evidence

ORD record
ord-4f2db855038747fd9d4ccf0efe31a871
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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