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

HRID 1707958

Reaction equation

HRID 1707958 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(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. [α]D26° =+79° (methylene chloride).

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-e87e17fc48394bcf90ac0eaba55d3752
Source dataset
uspto-grants-1994_10
Patent number
US05356885

Linked notes

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