Sodium Chloride → HCID 54124917, compound

HRID 359371Notes

Reaction equation

HRID 359371 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH3:9][C:10]1([CH3:17])[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:9][C:10]1([CH3:17])[C:14](=[O:15])[CH:13]=[C:12]([CH:16]=[CH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[O:11]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-

Product 1

HCID 54124917HCID 54124917, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-pyridinecarboxaldehyde (1.1 g, 9.9 mM) and 2,2,5-trimethyl-3(2H)-furanone (1.5 g, 11.9 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (1.2 mL, 1.2 mM). The reaction solution was stirred at room temperature for 2 days. After saturated aqueous sodium chloride (400 mL) was added, the aqueous layer was extracted with diethyl ether (3×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give a brown solid. The residue was purified by chromatography (silica gel, pet. ether/ethyl acetate) to yield yellow crystals (1.6 g, 75% yield), m.p. 87.5°-89.0° C.

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether (3×100 mL)
  2. washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a brown solid
  7. customThe residue was purified by chromatography (silica gel, pet. ether/ethyl acetate)

Sources & evidence

ORD record
ord-08d72ebe838448f9a6451c746e533f36
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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