Sodium Carbonate → 5-Methoxy-2-(3-pyridyl)-oxazole

HRID 1650702Notes

Reaction equation

HRID 1650702 reaction equation
[CH3:1][O:2][C:3]([CH2:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[N:10][CH:9]=1)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)([O-])[O-].[Na+].[Na+].CO.CCOCC>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]1[O:14][C:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14812Phosphorus oxide (P4O10)HCID 521804Glycine, N-(3-pyridinylcarbonyl)-, methyl esterHCID 21864698Diethyl ether methanol

Product 1

HCID 196125095-Methoxy-2-(3-pyridyl)-oxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of 19.0 g (0.100 mol) of 77 in 300 ml of dry chloroform was refluxed under vigorous stirring with 40 g of P2O5 for 24 h. The mixture was filtered after cooling. The filtrate was evaporated in vacuo leaving a red oil. The precipitate was dissolved in water at 0°-5° C. and the aqueous solution made basic with sodium carbonate. Extraction with 3×200 ml of dichloromethane, drying of the combined organic phases over magnesium sulphate, and removal of the solvent in vacuo gave a red oil which was combined with the above mentioned oil obtained from the chloroform phase. The oil was applied to a silica gel column (eluent; methanol/ether=1/19) giving a colorless oil, 78. Yield: 5.9 g (0.034 mol, 34%).

Workup

  1. filtrationThe mixture was filtered
  2. temperatureafter cooling
  3. customThe filtrate was evaporated in vacuo
  4. customleaving a red oil
  5. extractionExtraction with 3×200 ml of dichloromethane
  6. dry with materialdrying of the combined organic phases over magnesium sulphate, and removal of the solvent in vacuo
  7. customgave a red oil which
  8. customgiving a colorless oil, 78

Sources & evidence

ORD record
ord-90ac642a6adb418b88a8b5e2a6cba3b3
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

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