Hydrochloric Acid → Methyl 3-(nitromethyl)hexanoate

HRID 1453909

反応式

HRID 1453909 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 22928669Methyl 3-(nitromethyl)hexanoate収率 53.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-4108802d4c004e8394dee1da3852c21a
出典データセット
uspto-grants-2009_01
特許番号
US07476688B2

関連ノート

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