Tetrahydrofuran → HCID 18969211, compound

HRID 398839Notes

Reaction equation

HRID 398839 reaction equation
CC(C)([O-])C.[K+].O1CCCC1.[CH:12]1([C:18]([C:20]2[C:21]([N:26]([CH2:30][CH3:31])[C:27](=[O:29])[CH3:28])=[N:22][CH:23]=[CH:24][CH:25]=2)=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>O>[CH:12]1([C:18]2[C:20]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:26]([CH2:30][CH3:31])[C:27](=[O:29])[CH:28]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18969122HCID 18969122, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18969211HCID 18969211, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 2.9 g of 90% potassium tert-butoxide was added to 70 ml of tetrahydrofuran solution containing 6.4 g of N-(3-cyclohexylcarbonyl-2-pyridyl)-N-ethylacetamide, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was mixed with water and extracted with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate) to give 4.5 g of 4-cyclohexyl-1-ethyl-1,8-naphthyridin-2(1H)-one.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialthe resulting organic layer was dried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (toluene-ethyl acetate)

Sources & evidence

ORD record
ord-90e1cfd6d5e74d6a9c8c8bb3ce9d5533
Source dataset
uspto-grants-1998_10
Patent number
US05817670

Reaction notes

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