Sodium Chloride → (S)-3-Hept-6-enoyl-4-isopropyl-oxazolidin-2-one

HRID 1740482Notes

Reaction equation

HRID 1740482 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)([CH3:3])[CH3:2].[Li]CCCC.[C:15](Cl)(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].[Na+].[Cl-]>C1COCC1.CCCCCC>[C:15]([N:5]1[C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:8][O:7][C:6]1=[O:9])(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 108556156-Heptenoyl chlorideHCID 178418339Butyllithium

Product 1

HCID 11053746(S)-3-Hept-6-enoyl-4-isopropyl-oxazolidin-2-oneYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 2.08 g (16.10 mmol, 1 equivalent) of (4S)-4-isopropyl-oxazolidin-2-one in 15 ml of THF is cooled to -78° C. and mixed drop by drop with 11.6 ml (18.52 mmol, 1.15 equivalents) of a 1.6 M solution of n-BuLi solution in hexane. Then, a solution of 2.95 g (20.13 mmol, 1.25 equivalents) of hept-6-enoyl chloride in 10 ml of THF is added at -78° C. It is allowed to heat to room temperature, and the reaction solution is poured onto saturated NaCl solution. The aqueous phase is extracted with ether, the combined organic phases are dried on MgSO4, and the solvent is distilled off in a rotary evaporator. The residue is purified by column chromatography with PE:DE=3:1. 3.55 g (14.82 mmol, 92%) of oxazolidinone 21 is obtained as a colorless oil.

Workup

  1. extractionThe aqueous phase is extracted with ether
  2. customthe combined organic phases are dried on MgSO4
  3. distillationthe solvent is distilled off in a rotary evaporator
  4. customThe residue is purified by column chromatography with PE

Sources & evidence

ORD record
ord-1214ff42a314462abcf64f3d3268d0bf
Source dataset
uspto-grants-1999_10
Patent number
US05969145

Reaction notes

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