Water → (S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-one

HRID 1464812Notes

Reaction equation

HRID 1464812 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH2:19]([O:21][CH2:22][C:23](Cl)=[O:24])[CH3:20].O>O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:23](=[O:24])[CH2:22][O:21][CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84189Ethoxyacetyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10825429(S)-4-Benzyl-3-(ethoxyacetyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of (S)-4-benzyloxazolidin-2-one (4.4 g, 25 mmol) in dry tetrahydrofuran (20 ml), cooled to -78° C., was added n-butyllithium (2.5M solution in hexane, 10 ml, 25 mmol) dropwise. Another 20 ml of tetrahydrofuran was added to facilitate stirring. A solution of ethoxyacetyl chloride (3.0 g, 25 mmol) in tetrahydrofuran (5 ml) was added and the mixture was stirred at -78° C. for 30 minutes, then warmed to room temperature, poured into water and extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried over sodium sulfate and concentrated to a yellow oil (4.3 g, [α]D =56.7°).

Workup

  1. stirringthe mixture was stirred at -78° C. for 30 minutes
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a yellow oil (4.3 g, [α]D =56.7°)

Sources & evidence

ORD record
ord-298c2c232698428790b80d41477fc4ed
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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