Hydrochloric Acid → Methyl 3-(nitromethyl)hexanoate

HRID 1453909

Reaction equation

HRID 1453909 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].N12CCCN=C1CCCCC2.[C:16]([O:23][CH3:24])(=[O:22])/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21].Cl>C(#N)C>[N+:1]([CH2:4][CH:18]([CH2:19][CH2:20][CH3:21])[CH2:17][C:16]([O:23][CH3:24])=[O:22])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5364409Methyl 2-hexenoate, (2E)-

Product 1

HCID 22928669Methyl 3-(nitromethyl)hexanoateYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Nitromethane (2.54 ml, 46 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.4 ml, 36 mmol) were added to a solution of methyl (E)-2-hexenoate (4.62 g, 36 mmol) in acetonitrile (20 ml) and the reaction mixture was stirred at room temperature for 14 hours. The reaction mixture was acidified by addition of a 1N HCl aqueous solution and then extracted with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (3.64 g) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.92 (3H, t, J=0.8 Hz), 1.29-1.48 (4H, m), 2.45 (2H, d, J=6.4 Hz), 2.57-2.68 (1H, m), 3.69 (3H, s), 4.43 (1H, dd, J=14.0 Hz, 6.0 Hz), 4.50 (1H, dd, J=14.0, 6.8 Hz)

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing the organic layer with brine
  3. dry with materialdrying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4108802d4c004e8394dee1da3852c21a
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Linked notes

Loading…