Water → Dimethyl 2-methyl-2-(4-nitrophenyl)malonate

HRID 2356688노트

반응식

HRID 2356688 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:21]I.O>O1CCCC1.C(OCC)(=O)C>[CH3:21][C:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2764303Dimethyl 2-(4-nitrophenyl)malonate

생성물 1

HCID 1485451Dimethyl 2-methyl-2-(4-nitrophenyl)malonate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

640 mg of compound 229.1 were dissolved in 12 ml of dry tetrahydrofuran and admixed with 138 mg of sodium hydride (60% in mineral oil). The mixture was stirred at room temperature for one hour, then a solution of 393 μl of methyl iodide in 5 ml of dry tetrahydrofuran was added dropwise and the resulting mixture was stirred at room temperature overnight. For workup, the reaction mixture was admixed cautiously with water and ethyl acetate. The organic phase was removed, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography (silica gel; n-heptane/0-10% ethyl acetate). Dimethyl 2-methyl-2-(4-nitrophenyl)malonate (231.1) was obtained; 1H NMR: 8.22, d, 2H, 7.61, d, 2H, 3.71, s, 6H, 1.82, s, 3H.

후처리

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe organic phase was removed
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (silica gel; n-heptane/0-10% ethyl acetate)

출처 및 근거

ORD 기록
ord-6176a00ba33d4939a2986cbfa35bb89a
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759366B2

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