Dimethyl malonate → Dimethyl 2-methoxycarbonyl-6-nitrophenylmalonate

HRID 428255

반응식

HRID 428255 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 2.1 g of sodium hydride in 15 mL of DMSO. The reaction mixture was then stirred at 100° C. for 1.0 h and then cooled to room temperature. 2-Chloro-3-methoxycarbonylnitrobenzene (2.15 g) was added to the above mixture in one portion and the mixture was heated to 100° C. for 1.5 h. 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. temperaturethe mixture was heated to 100° C. for 1.5 h
  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-8e56e89d0240438e9e84031caf05f037
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313158B1

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