Dimethylformamide → HCID 21833074, compound

HRID 1740794Notes

Reaction equation

HRID 1740794 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[Si:13]([CH2:20]CI)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])C.[C:23](=[O:26])([O-])[O-].[K+].[K+].[CH3:29]N(C)C=O>>[Si:13]([O:26][CH2:23][CH2:29][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:20]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 21833113HCID 21833113, compound

Product 1

HCID 21833074HCID 21833074, compoundYield 74%

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 3-nitrophenol (5 g, 36 mmol) in dimethylformamide (100 ml) at 0° C. was added sodium hydride (1.029 g, 34.4 mmol). After effervescence had subsided 1-t-butyldimethylsilyl-2-iodoethane was added (10.811 g, 37.8 mmol) and the reaction mixture left at room temperature for 18 hours. Potassium carbonate (2 g) was added and the mixture heated at 100° C. for 2 h. It was then quenched with saturated aqueous ammonium chloride solution and evaporated under reduced pressure. The residue was then partitioned between water and ethyl acetate and the organic extract washed with saturated aqueous sodium chloride solution twice, before being separated, dried, and evaporated under reduced pressure to give the crude product as a brown oil (9.697 g, 91%). This was chromatographed on silica eluting with 0-15% ethyl acetate/petroleum ether to give the product as a yellow oil (7.918 g, 74%)

Workup

  1. additionwas added (10.811 g, 37.8 mmol)
  2. customIt was then quenched with saturated aqueous ammonium chloride solution
  3. customevaporated under reduced pressure
  4. customThe residue was then partitioned between water and ethyl acetate
  5. extractionthe organic extract
  6. washwashed with saturated aqueous sodium chloride solution twice
  7. custombefore being separated
  8. customdried
  9. customevaporated under reduced pressure
  10. customto give the crude product as a brown oil (9.697 g, 91%)
  11. customThis was chromatographed on silica eluting with 0-15% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-adc55c1f0d96495ea22b1c8283018ff5
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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