Sodium hydride → 5-(3-Fluorophenyl)morpholin-3-one

HRID 1890670Notes

Reaction equation

HRID 1890670 reaction equation
Cl[CH2:2][C:3]([NH:5][CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=1)[CH2:7][OH:8])=[O:4].[H-].[Na+]>C1COCC1>[F:15][C:11]1[CH:10]=[C:9]([CH:6]2[NH:5][C:3](=[O:4])[CH2:2][O:8][CH2:7]2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 583359312-chloro-N-(1-(3-fluorophenyl)-2-hydroxyethyl)acetamide

Product 1

HCID 583357985-(3-Fluorophenyl)morpholin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In step 2-3, a solution of 2-chloro-N-(1-(3-fluorophenyl)-2-hydroxyethyl)acetamide (5.5 g, 24 mmol) in THF (150 mL) was slowly added to a suspension of NaH (1.05 g, 26 mmol) in THF (600 mL) at 0° C. The heterogeneous solution was warmed to room temperature and stirred overnight. The reaction mixtures was quenched, concentrated and ethyl acetate was added to the residue. This solution was washed with water and brine and the organic phase was dried over MgSO4, filtered and concentrated to yield 5-(3-fluorophenyl)morpholin-3-one (2-3).

Workup

  1. customThe reaction mixtures
  2. customwas quenched
  3. concentrationconcentrated
  4. additionethyl acetate was added to the residue
  5. washThis solution was washed with water and brine
  6. dry with materialthe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7eb810cdbd964038a132a13ba3a076e7
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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