Water → pentan-3-one O-(2-nitrophenyl)oxime

HRID 342410

Reaction equation

HRID 342410 reaction equation
[CH3:1][CH2:2][C:3](=[N:6][OH:7])[CH2:4][CH3:5].[H-].[Na+].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].O>CN(C)C=O>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:7][N:6]=[C:3]([CH2:4][CH3:5])[CH2:2][CH3:1])([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 28017453-Pentanone oxime

Product 1

HCID 53768417pentan-3-one O-(2-nitrophenyl)oximeYield 111.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of pentan-3-one oxime (6.00 g) in dimethylformamide (30 ml) was added sodium hydride (60% oil suspension, 2.37 g) under ice cooling. After 15 minutes, to the above mixture was added dropwise 1-fluoro-2-nitrobenzene (5.98 g) in dimethylformamide (30 ml). The mixture was stirred for 3 hours at ambient temperature and poured into a mixture of ice and water. The separated oil was extracted with diethyl ether. The organic layer was washed with water, dried over sodium sulfate and evaporated in vacuo to give pentan-3-one O-(2-nitrophenyl)oxime (10.51 g) as a brown oil.

Workup

  1. extractionThe separated oil was extracted with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-639adc713648416286868651f74f44a8
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Linked notes

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