Sodium hydride → HCID 18623221, compound

HRID 1860397Notes

Reaction equation

HRID 1860397 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]([NH:7][CH:8]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1)[CH2:9][OH:10])=[O:6]>C1COCC1>[F:18][C:13]1[CH:12]=[C:11]([CH:8]2[NH:7][C:5](=[O:6])[CH2:4][O:10][CH2:9]2)[CH:16]=[CH:15][C:14]=1[F:17]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 186232362-Chloro-N-[1-(3,4-difluorophenyl)-2-hydroxy-ethyl]-acetamide

Product 1

HCID 18623221HCID 18623221, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (0.29 g, 11.39 mmol) in 48 mL THF was added a solution of 2-chloro-N-[1-(3,4-difluoro-phenyl)-2-hydroxy-ethyl]-acetamide (2.6 g, 10.4 mmol) in 48 mL THF dropwise via a dropping funnel at −25° C. over 20 min. After the addition was over, the cooling bath was removed and the reaction mixture was stirred at room temperature for 8 hours. TLC analysis indicated a complete disappearance of the starting material. The reaction was quenched by adding a few crystals of ice. It was extracted thoroughly with EtOAc (3×30 mL) and was washed with brine. The organic layer was separated and dried over MgSO4. The organic layer was filtered and the solvent was removed in vacuo. The residue was suspended in EtOAc and the white solid was collected via filtration which was found to be 5-(3,4-difluoro-phenyl)-morpholin-3-one (0.8 g, 38% yield).

Workup

  1. additionAfter the addition
  2. customwas removed
  3. customThe reaction was quenched
  4. additionby adding a few crystals of ice
  5. extractionIt was extracted thoroughly with EtOAc (3×30 mL)
  6. washwas washed with brine
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationThe organic layer was filtered
  10. customthe solvent was removed in vacuo
  11. filtrationthe white solid was collected via filtration which

Sources & evidence

ORD record
ord-f451693624bf4881a0e8128c9b65b3e4
Source dataset
uspto-grants-2003_03
Patent number
US06531471B2

Reaction notes

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