Tetrahydrofuran → 3-(2-Fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1h)-pyridone

HRID 1385930Notes

Reaction equation

HRID 1385930 reaction equation
C1COCC1.[H-].[Na+].[C:8]([O:12][CH3:13])(=[O:11])[CH2:9][OH:10].[F:14][C:15]1[CH:20]=[C:19](F)[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:16]=1[C:25]1[C:26](=[O:36])[N:27]([CH3:35])[C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=1>O>[F:14][C:15]1[CH:20]=[C:19]([O:10][CH2:9][C:8]([O:12][CH3:13])=[O:11])[C:18]([N+:22]([O-:24])=[O:23])=[CH:17][C:16]=1[C:25]1[C:26](=[O:36])[N:27]([CH3:35])[C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 154570533-(2,4-difluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone

Product 1

HCID 154570543-(2-Fluoro-4-methoxycarbonylmethoxy-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2(1h)-pyridoneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 20 ml of THF, 0.24 g (60 mmol) of 60% sodium hydride was suspended under cooling with ice, and 0.32 g (6.6 mmol) of methyl glycolate, was added thereto, followed by stirring for 15 minutes. To this mixture, 2 g (6.0 mmol) of 3-(2,4-difluoro-5-nitrophenyl)-1-methyl-6-trifluormethyl-2(1H)-pyridone was added, followed by stirring at room temperature for 3 hours. The product was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. After distilling off ethyl acetate under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain 1.57 g (yield: 65%) of the desired product. 1H-NMR (400 MHz, CDCl3) δ value: 3.70(3H,s), 3.84(3H,s), 4.81(2H,s), 6.76(1H,d), 6.78(1H,d), 7.53(1H,d), 8.26(1H,d)ppm.

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 3 hours
  3. extractionextracted with ethyl acetate
  4. washAfter washing with water
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off ethyl acetate under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-02be106e0a1842d09d692dc437130528
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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