Tetrahydrofuran → (S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

HRID 2399893Notes

Reaction equation

HRID 2399893 reaction equation
[CH3:1][CH:2]([CH:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].C([Li])CCC.[CH2:15](Cl)[CH2:16][CH2:17][CH:18]=[CH2:19].[O:21]1CCCC1>CCCCCC.[Cl-].[NH4+].C(OCC)C>[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:15](=[O:21])[CH2:16][CH2:17][CH:18]=[CH2:19])[CH3:3]

Participants

8

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 5193532-Oxazolidinone, 4-(1-methylethyl)-HCID 5230425-Chloro-1-penteneHCID 178418339Butyllithium

Product 1

HCID 11820460(S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a -78° C. solution of 5.0 g of 4-(1-methylethyl)-2-oxazolidinone in 80 ml of tetrahydrofuran is added, dropwise, 15.5 ml of 2.5M n-butyl lithium in hexane. After stirring for 30 minutes, a solution of 4.8 g of 4-pentenyl chloride in 30 ml of tetrahydrofuran is added, dropwise, and the resulting solution is stirred at -78° C. for 3.5 hours. The reaction is diluted with aqueous ammonium chloride and diethyl ether. The organic layer is washed with water, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether) to give 5.8 g of the desired product as a pale yellow oil.

Workup

  1. stirringdropwise, and the resulting solution is stirred at -78° C. for 3.5 hours
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-5fc9f1701d944457b40192659c8f3fa2
Source dataset
uspto-grants-1995_09
Patent number
US05451685

Reaction notes

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