Hydrochloric Acid → Methyl 3-(nitromethyl)hexanoate

HRID 1453909

반응식

HRID 1453909 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 22928669Methyl 3-(nitromethyl)hexanoate수율 53.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-4108802d4c004e8394dee1da3852c21a
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476688B2

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