Sodium Chloride → HCID 18658185, compound

HRID 1768583Notes

Reaction equation

HRID 1768583 reaction equation
C([Li])CCC.[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:19]1([CH2:29][CH2:30][C:31](Cl)=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.[Cl-].[Na+]>CCCCCC.O1CCCC1>[C:19]1([CH2:29][CH2:30][C:31]([N:14]2[C@@H:13]([CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:17][O:16][C:15]2=[O:18])=[O:32])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 14429451HCID 14429451, compoundHCID 178418339Butyllithium

Product 1

HCID 18658185HCID 18658185, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

14.8 mmole of butyllithium in hexane were added dropwise to a solution of 2.63 g (14.8 mmole) of (S)-(-)-4-benzyl-2-oxazolidinone dissolved in 50 ml of anhydrous tetrahydrofuran at -78° C. under an atmosphere of nitrogen. The mixture was stirred for 30 minutes at this temperature, and then 2.95 g (13.5 mmole) of 1-naphthylpropionyl chloride in 15 ml of anhydrous tetrahydrofuran were slowly added dropwise at the same temperature=the mixture was then stirred for 3 hours. At the end of this time, a saturated aqueous solution of sodium chloride was added to the mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then freed from the solvent by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: a 1: 4 by volume mixture of ethyl acetate and hexane), to afford 4.65 g (96%) of the title compound as a white amorphous substance.

Workup

  1. stirringwas then stirred for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customfreed from the solvent by evaporation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent
  6. additiona 1: 4 by volume mixture of ethyl acetate and hexane),

Sources & evidence

ORD record
ord-ca0e6aa242434bbb89a4aeb2e42021fd
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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