Sodium hydride → HCID 22049033, compound

HRID 1167717Notes

Reaction equation

HRID 1167717 reaction equation
[H-].[Na+].C([O:7][C:8](=[O:22])[NH:9][CH:10]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=1)[CH2:11]O)(C)(C)C>C1COCC1>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[F:20])[CH2:13][CH:10]1[CH2:11][O:22][C:8](=[O:7])[NH:9]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 22048830Carbamic acid, [2-(3,4-difluorophenyl)-1-(hydroxymethyl)ethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 22049033HCID 22049033, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

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 50 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=0.25, 3:2 hexane-EtOAc)

Sources & evidence

ORD record
ord-d105b0e2e5ad4e43a15669c86e00f58c
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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