Fluoride Ion → 5-Ethynyl-4-methyl-3-nitro-2-pyridone

HRID 1387276Notes

Reaction equation

HRID 1387276 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:8]([CH3:17])=[C:9]([N+:14]([O-:16])=[O:15])[C:10](=[O:13])[NH:11][CH:12]=1)(C)C.[F-]>C1COCC1.C(OCC)(=O)C>[C:6]([C:7]1[C:8]([CH3:17])=[C:9]([N+:14]([O-:16])=[O:15])[C:10](=[O:13])[NH:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 2

HCID 28179Fluoride IonHCID 217064915-Trimethylsilylethynyl-4-methyl-3-nitro-2-pyridone

Product 1

HCID 217064835-Ethynyl-4-methyl-3-nitro-2-pyridoneYield 37.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-trimethylsilylethynyl-4-methyl-3-nitro-2-pyridone (1.0 g, 2.7 mmol) in THF (10 mL) was added tetrabutylammoniun fluoride (1M in THF, 2 mL). After 30 minutes the mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. Chromatography of the residue over silica gel (40% ethyl acetate/hexane) gave 5-ethynyl-4-methyl-3-nitro-2-pyridone (0.18 g, 22%).

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-03f72c7b0e8c4a5f976b80856cdbb0bc
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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