Water → HCID 14977438, compound

HRID 1032955Notes

Reaction equation

HRID 1032955 reaction equation
[H-].[Na+].C[C:4]1[C:5]([N+:11]([O-:13])=[O:12])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH3:14][O:15][CH2:16]Cl.O.[CH3:19]N(C=O)C>>[CH3:14][O:15][CH2:16][O:10][C:6]1[CH:7]=[CH:8][C:9]([CH3:19])=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 210263-Methyl-2-nitrophenolHCID 24758Sodium hydride

Product 1

HCID 14977438HCID 14977438, compound

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% in oil, 4.78 g, 0.12 -methyl-2-nitrophenol (known compound) (15.6 g, 0.102 mol) in DMF (50 ml) under nitrogen atmosphere under ice-cooling over a period of 30 minutes. The mixture was stirred at 0° C. for 30 minutes, and thereto was added dropwise chloromethyl methyl ether (9.3 ml, 0.122 mol). The reacion mixture was stirred at 0° C. for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The concentrate was purified by column chromatography to give the ether compound (1). Yield 20.1 g (100%).

Workup

  1. temperaturecooling over a period of 30 minutes
  2. stirringThe reacion mixture was stirred at 0° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe concentrate was purified by column chromatography
  8. customto give the ether compound (1)

Sources & evidence

ORD record
ord-b5285b61c3f244aea5cccd73d05889b6
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

Loading…