Nitromethane → HCID 66803796, compound

HRID 1500141Notes

Reaction equation

HRID 1500141 reaction equation
[CH2:1]([C:3]1[CH2:4][CH:5]2[CH:8]([CH:9]=1)[C:7](=[CH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]2)[CH3:2].N12CCCN=C1CCCCC2.P([O-])(O)(O)=O.[K+].[N+:35]([CH3:38])([O-:37])=[O:36]>>[CH2:1]([C:3]1[CH2:4][CH:5]2[CH:8]([CH:9]=1)[C:7]([CH2:10][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])([CH2:38][N+:35]([O-:37])=[O:36])[CH2:6]2)[CH3:2]

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516951Monobasic potassium phosphateHCID 66696968HCID 66696968, compound

Product 1

HCID 66803796HCID 66803796, compound

Conditions

Temperature
55 °C

Procedure

Tert-butyl 3-ethylbicyclo[3.2.0]hept-3-en-6-ylideneacetate (1.32 g, 5.63 mmol) was dissolved in nitromethane (7 mL). To the solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (1.2 mL, 7.3 mmol) was added, and the mixture was heated with stirring at 50 to 60° C. for 7 hours. The mixture was allowed to cool, and a saturated aqueous solution of potassium dihydrogen phosphate was then added thereto, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil substance (1.39 g, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain the compound of interest as a colorless oil substance (1.39 g, 84%)

Sources & evidence

ORD record
ord-0cd89d7ae0654940b4fdc0eeb99039eb
Source dataset
uspto-grants-2015_12
Patent number
US09206104B2

Reaction notes

Loading…