Nitromethane → Ethyl 5-methyl-3-nitromethylheptanoate

HRID 130517Notes

Reaction equation

HRID 130517 reaction equation
[CH3:1][CH:2]([CH2:11][CH3:12])[CH2:3][CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C1CCN2C(=NCCC2)CC1.[N+:24]([CH3:27])([O-:26])=[O:25]>C(#N)C>[CH3:1][CH:2]([CH2:11][CH3:12])[CH2:3][CH:4]([CH2:27][N+:24]([O-:26])=[O:25])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53937332Ethyl 5-methyl-2-heptenoate

Product 1

HCID 21888385Ethyl 5-methyl-3-nitromethylheptanoateYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 5-methyl-2-heptanoate 12 (6.75 g, 39.70 mmol), DBU (6.0 g, 39.7 mmol), nitromethane (21.97 g, 359.9 mmol) in acetonitrile 80 mL was stirred at room temperature under nitrogen atmosphere overnight. The mixture was concentrated to an oil. A solution of the oil in ether was washed with 1N HCl, brine and dried. It was evaporated to give a light oil which was chromatographed on silica gel, eluting with 5% to 10% ether in Pet. ether to give 13 (3.6 g, 42%). 1H-NMR (CDCl3) δ 4.49-4.39 (m), 4.12-4.07 (m), 3.61 (m), 2.36 (m), 1.36-1.18 (m), 0.86-0.79.

Workup

  1. concentrationThe mixture was concentrated to an oil
  2. washA solution of the oil in ether was washed with 1N HCl, brine
  3. customdried
  4. customIt was evaporated
  5. customto give a light oil which
  6. customwas chromatographed on silica gel
  7. washeluting with 5% to 10% ether in Pet. ether

Sources & evidence

ORD record
ord-6f5103e49af74faf909929834ae2957f
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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