Dimethyl malonate → Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate

HRID 24441

반응식

HRID 24441 반응식
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]>CS(C)=O>[CH3:22][O:21][C:19]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:23]([O-:25])=[O:24])[C:13]=1[CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[O:20]

참가 물질

5

반응물 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 10751184Methyl 2-chloro-3-nitrobenzoate

생성물 1

HCID 54355276Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

Dimethyl malonate (6.0 ml) was added to an ice-cold suspension of sodium hydride (2.1 g) in dimethylsulfoxide (15 ml). The reaction mixture was heated to 100° C., stirred for 1 hour and then cooled to room temperature. 2-Chloro-3-methoxycarbonylnitrobenzene (2.15 g) was added in one portion and the mixture was stirred at 100° C. for 1.5 hour. The reaction mixture was then cooled to room temperature and poured into ice water, acidified to pH 5, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated to give 3.0 g of the dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate.

후처리

  1. temperaturecooled to room temperature
  2. stirringthe mixture was stirred at 100° C. for 1.5 hour
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ccbe698d28b142d09fe9146b2e53ddaf
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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