Nitromethane → Tert-butyl [6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

HRID 2190981Notes

Reaction equation

HRID 2190981 reaction equation
[CH:1]12[CH2:7][C:6](=[CH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]1[CH:4]=[CH:3][CH2:2]2.N12CCCN=C1CCCCC2.[N+:27]([CH3:30])([O-:29])=[O:28]>Cl>[N+:27]([CH2:30][C:6]1([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7][CH:1]2[CH:5]1[CH:4]=[CH:3][CH2:2]2)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66697018Tert-butyl bicyclo[3.2.0]hept-3-en-6-ylideneacetate

Product 1

HCID 66803873Tert-butyl [6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Tert-butyl bicyclo[3.2.0]hept-3-en-6-ylideneacetate (1.73 g, 8.39 mmol) was dissolved in nitromethane (10 mL). To the solution, 1,8-diazabicyclo[5.4.0]undec-7-ene (1.3 mL, 8.4 mmol) was added, and the mixture was stirred at room temperature for 1 hour and then heated with stirring at 50 to 60° C. for 5 hours. The mixture was allowed to cool and then diluted with 1 N hydrochloric acid and saturated saline, 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 (1.98 g, 89%).

Workup

  1. temperatureheated
  2. stirringwith stirring at 50 to 60° C. for 5 hours
  3. temperatureto cool
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. customto obtain the compound of interest as a colorless oil substance (1.98 g, 89%)

Sources & evidence

ORD record
ord-c377fd099a4041939f8a3c4af58f0efb
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

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