Ethyl Acetate → HCID 11428608, compound

HRID 2116616Notes

Reaction equation

HRID 2116616 reaction equation
[Na+].[Br:2][C:3]1[CH:17]=[CH:16][C:6]([CH:7]=[N:8][CH:9]([CH:13]([CH3:15])[CH3:14])[C:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.[C:18](Cl)(=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22].C(OCC)(=O)C>ClCCl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]2[N:8]([C:18](=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH:9]([CH:13]([CH3:15])[CH3:14])[C:10](=[O:12])[O:11]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 61186Valeryl chlorideHCID 69185427HCID 69185427, compound

Product 1

HCID 11428608HCID 11428608, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

12.6 g of 2-[(4-bromobenzylidene)amino]-3-methylbutyric acid sodium salt (41.1 mmoles) are suspended in 80 ml of dry dichloromethane. The mixture is refluxed (40° C.), under slight nitrogen stream. 7.9 g of valeryl chloride (65.5 mmoles) are added. After 2 hours under reflux, the mixture is cooled to 25° C. The organic phase is washed three times with 50 ml of water and concentrated under reduced pressure, at 25-30° C., to obtain an oily residue. 50 ml of ethyl acetate are added and the organic phase is washed with a weakly basic NaOH solution and/or with water to neutrality. The organic phase is washed with a sodium bisulfite solution. The organic phase is washed with water and dried over sodium sulfate, filtered and evaporated under reduced pressure. The oily residue is taken up with ethanol from which the product crystallizes as a white solid. 2-(4-Bromophenyl)-4-isopropyl-3-pentanoyl-oxazolidin-5-one is obtained (5.2 g; 14.1 mmoles; molar yield: 34%).

Workup

  1. temperatureAfter 2 hours under reflux
  2. temperaturethe mixture is cooled to 25° C
  3. washThe organic phase is washed three times with 50 ml of water
  4. concentrationconcentrated under reduced pressure, at 25-30° C.
  5. customto obtain an oily residue
  6. washthe organic phase is washed with a weakly basic NaOH solution
  7. washThe organic phase is washed with a sodium bisulfite solution
  8. washThe organic phase is washed with water
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated under reduced pressure
  12. customcrystallizes as a white solid

Sources & evidence

ORD record
ord-2ccadb3ab97a4797bdbce53d333f0535
Source dataset
uspto-grants-2008_10
Patent number
US07439261B2

Reaction notes

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