Diethyl Malonate → Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate

HRID 1435937노트

반응식

HRID 1435937 반응식
[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:13]([O:21][CH2:22][CH3:23])=[O:20]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 516892Sodium BicarbonateHCID 135735673-Methyl-2-nitrobenzaldehyde

생성물 1

HCID 68898055Diethyl 2-(3-methyl-2-nitrobenzylidene)malonate수율 90.8%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

반응 조건

온도
100 °C

실험 절차

To a solution of this aldehyde (10.0 g, 60.6 mmol) in 20 mL of acetic anhydride was added diethyl malonate (9.7 g, 60.6 mmol) and sodium bicarbonate (7.6 g, 91 mmol). The reaction mixture was stirred at 100° C. for 24 h. The reaction was allowed to cool and then was partitioned between ethyl acetate and water. The organics were washed sequentially with water, aq sat'd NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 16.9 g (90%) of the title compound.

후처리

  1. temperatureto cool
  2. customwas partitioned between ethyl acetate and water
  3. washThe organics were washed sequentially with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-5ad771bd5b564352bf233dcaab2d6fed
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618980B2

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