Propionyl chloride → Propionyl Oxazolidinone

HRID 414357Notes

Reaction equation

HRID 414357 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([Li])CCC.[C:12](Cl)(=[O:15])[CH2:13][CH3:14]>CCCCCC>[C:12]([N:3]1[CH2:4][CH2:5][O:1][C:2]1=[O:6])(=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 739492-Oxazolidinone2×HCID 178418339Butyllithium

Product 1

HCID 641554Propionyl Oxazolidinone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following the cyclization reaction, the formed oxazolidinone is N-acylated to form the nucleophilic precursor of the molecule. The oxazolidinone is reacted with butyllithium in hexane, to form the conjugate base and then reacted with an acyl halide such as propionyl chloride at -71° C., for 0.5-1 hour to yield the N-propionyloxazolidinone.

Workup

  1. customthe cyclization reaction
  2. customto form the nucleophilic precursor of the molecule
  3. customto form the conjugate base

Sources & evidence

ORD record
ord-1c2084addbcf4a2fa795a1edf0ddad25
Source dataset
uspto-grants-1988_12
Patent number
US04791207

Reaction notes

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