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

HRID 2356688ノート

反応式

HRID 2356688 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6176a00ba33d4939a2986cbfa35bb89a
出典データセット
uspto-grants-2010_07
特許番号
US07759366B2

反応ノート

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