Hexane → (S)-4-benzyl-3-pentanoyloxazolidin-2-one

HRID 1695026Notes

Reaction equation

HRID 1695026 reaction equation
C([Li])CCC.CCCCCC.[CH2:12]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[NH:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:25][CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].[Cl-].[NH4+]>O1CCCC1>[CH2:12]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[N:20]1[C:29](=[O:30])[CH2:28][CH2:27][CH2:26][CH3:25])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 61186Valeryl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 11391341(S)-4-benzyl-3-pentanoyloxazolidin-2-oneYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

90 ml of a solution of n-butyllithium in n-hexane (1.60 mol/l) (144 mmol) was added to a solution of 25.0 g of (S)-4-benzyl-2-oxazolidinone (141 mmol) in tetrahydrofuran (600 ml) under a nitrogen atmosphere and at −78° C. over 10 minutes, and the mixture was stirred at the same temperature for 20 minutes. Then, 19.0 ml of n-valeryl chloride (159 mmol) was added over 10 minutes. The mixture was stirred at the same temperature for 20 minutes and then further stirred at room temperature for three hours. 90 ml of a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was further stirred at room temperature for 15 minutes. The reaction mixture was concentrated under reduced pressure and diluted with 300 ml of water, followed by extraction with methylene chloride. Then, the organic layer was washed with a saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain 37.3 g of the crude title compound.

Workup

  1. stirringThe mixture was stirred at the same temperature for 20 minutes
  2. stirringfurther stirred at room temperature for three hours
  3. stirringthe mixture was further stirred at room temperature for 15 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additiondiluted with 300 ml of water
  6. extractionfollowed by extraction with methylene chloride
  7. washThen, the organic layer was washed with a saturated sodium bicarbonate aqueous solution and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-02c4a897613648eb8bbe3f42e35cd3bf
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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