Ethanol → 5-Nitro-(3-methoxyphenyl)-2-pentanone

HRID 233799Notes

Reaction equation

HRID 233799 reaction equation
CO[C:3]1[CH:4]=[C:5](C=[CH:12][CH:13]=1)[CH:6]=[CH:7][N+:8]([O-:10])=[O:9].[CH2:14]([O:16][C:17](=O)[CH:18]=[C:19](N1CCCC1)[CH3:20])C.C([OH:29])C>>[N+:8]([CH2:7][CH2:6][CH2:5][C:4](=[O:29])[CH2:3][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([O:16][CH3:14])[CH:12]=1)([O-:10])=[O:9]

Participants

4

Reactant 3

HCID 702EthanolHCID 2614113-Methoxy--nitrostyreneHCID 586690Ethyl 3-(1-pyrrolidinyl)-2-butenoate

Product 1

HCID 233580745-Nitro-(3-methoxyphenyl)-2-pentanone

Procedure

A mixture of 3-methoxynitrostyrene (6.96 g, 39 mmol) and ethyl-3-pyrrolidino-2-butenoate (7.10 g, 39 mmol) was refluxed in ethanol (100 mL) for 4.0 h. The solvent was then removed and the residue refluxed in 10% HCl (50 mL) for 2.0 h. After cooling to ambient temperature the reaction mixture was extracted with ethyl ether (3×25 mL). The extract was dried (MgSO4) and the solvent removed to yield 9.40 g of crude material as an oil. This was distilled twice using a Kugelrohr oven (225° C. C/0.4mm Hg) yielding 4.83 g of product. This was further purified by flash chromatography (n-hexane/ethyl acetate 1/1), yielding 3.25 g (35%) of a colorless oil.: MS (EI) m/e 237.15 (M+, 22), 190.05 (100), 175.05 (32), 149.05 (35), 148.05 (37), 134.05 (36), 115 (10, 20), 91.00 (28), 77.00 (21).

Workup

  1. customThe solvent was then removed
  2. temperaturethe residue refluxed in 10% HCl (50 mL) for 2.0 h
  3. extractionwas extracted with ethyl ether (3×25 mL)
  4. dry with materialThe extract was dried (MgSO4)
  5. customthe solvent removed
  6. customto yield 9.40 g of crude material as an oil
  7. distillationThis was distilled twice
  8. custom(225° C. C/0.4mm Hg)

Sources & evidence

ORD record
ord-e1778a60dfa144538bbd4b696d392162
Source dataset
uspto-grants-1997_01
Patent number
US05594024

Reaction notes

Loading…