Pyridine → HCID 69428138, compound

HRID 1295255Notes

Reaction equation

HRID 1295255 reaction equation
[OH:1][CH:2]([C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[N:17]1[CH:22]=CC=CC=1.[O:23]1CCCC1.C(Cl)(=O)OC1C=CC=CC=1>O>[O:23]=[C:22]1[N:17]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:2]([CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[O:1]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 15891Phenyl chloroformateHCID 22930709HCID 22930709, compound

Product 1

HCID 69428138HCID 69428138, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 4-hydroxy-5-oxo-5-phenylpentanoate (4.50 g), pyridine (1.80 ml) and tetrahydrofuran (30 ml) was slowly added phenyl chlorocarbonate (2.80 ml) at 0° C. and the mixture was stirred at room temperature for 2 hrs. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was dissolved in acetic acid (30 ml), ammonium acetate (7.79 g) was added and the mixture was refluxed for 3 hrs. The reaction mixture was concentrated and the obtained residue was dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and then saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography, and methyl 3-(2-oxo-4-phenyloxazolin-5-yl)propionate was obtained as colorless crystals (3.57 g, yield 71%) from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 104–105° C.

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe obtained residue was dissolved in acetic acid (30 ml)
  7. additionammonium acetate (7.79 g) was added
  8. temperaturethe mixture was refluxed for 3 hrs
  9. concentrationThe reaction mixture was concentrated
  10. dissolutionthe obtained residue was dissolved in ethyl acetate
  11. washwashed with saturated aqueous sodium hydrogen carbonate
  12. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-42c993d650e04a3d86556a8a8d71a940
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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