Tetrahydrofuran → (S)-4-(2-chlorophenyl)oxazolidin-2-one
Reaction equation
Cl.[NH2:2][C@@H:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])[CH2:4][OH:5].[OH-].[K+].C1C[O:18][CH2:17]C1.C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O.CCOC(C)=O>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C@H:3]1[CH2:4][O:5][C:17](=[O:18])[NH:2]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (S)-2-amino-2-(2-chlorophenyl)ethanol hydrochloride (500 mg, 2.40 mmol) in water (12 mL) at 0° C. was added potassium hydroxide (809 mg, 14.4 mmol) followed by THF (12 mL) and the reaction was stirred at 0° C. for 20 minutes. Bis(trichloromethyl) carbonate (713 mg, 2.40 mmol) was added and the reaction was stirred at 0° C. for 2 hours. The reaction was poured into EtOAc and the organic phase washed with 1N HCl, 1N NaOH and brine. The organic layer was dried over MgSO4, filtered and concentrated to provide (S)-4-(2-chlorophenyl)oxazolidin-2-one (265 mg, 55.8% yield) as an oil which solidified upon standing.
Workup
- stirringthe reaction was stirred at 0° C. for 2 hours
- washthe organic phase washed with 1N HCl, 1N NaOH and brine
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-dc85b0849b3947dbb0ca26f1e9c73165
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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