Sodium Chloride → HCID 53936569, compound

HRID 359374Notes

Reaction equation

HRID 359374 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3][CH:2]=1.[CH3:13][C:14]1([CH3:21])[C:18](=[O:19])[CH:17]=[C:16]([CH3:20])[O:15]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=[CH:20][C:16]2[O:15][C:14]([CH3:21])([CH3:13])[C:18](=[O:19])[CH:17]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 780724-QuinolinecarboxaldehydeHCID 1370803(2H)-Furanone, 2,2,5-trimethyl-

Product 1

HCID 53936569HCID 53936569, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-quinolinecarboxaldehyde (2.8 g, 17.8 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). After the reaction solution was stirred for 4 hours, 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 oil. The crude product was purified by column chromatography (silica gel, pet. ether-ethyl acetate) to yield a yellow crystalline solid (1.2 g, 32% yield), m.p. 117°-118° 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 oil
  7. customThe crude product was purified by column chromatography (silica gel, pet. ether-ethyl acetate)

Sources & evidence

ORD record
ord-6722f73cf34641a3adaa672f5fedc8fb
Source dataset
uspto-grants-1991_03
Patent number
US05001126

Reaction notes

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