Ethyl bromoacetate → Methyl 2-ethoxycarbonylmethoxy-3-nitrosalicylate

HRID 440670ノート

反応式

HRID 440670 の反応式
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[OH:14])([O-:3])=[O:2].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-:23].[K+].[K+].[Cl-].[Li+]>CN(C)C=O>[CH2:20]([O:19][C:17]([CH2:16][O:14][C:5]1([OH:23])[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=[CH:11][CH:6]1[C:7]([O:9][CH3:10])=[O:8])=[O:18])[CH3:21]

参加物

6

反応物 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 596904Methyl 2-hydroxy-3-nitrobenzoate

生成物 1

HCID 67734528Methyl 2-ethoxycarbonylmethoxy-3-nitrosalicylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

In a flask are placed 4.14 g (0.021 mole) of methyl 3-nitrosalicylate, 3.70 g (0.022 mole) of ethyl bromoacetate, 3.2 g (0.023 mole) of potassium carbonate, and 80 mL of N,N-dimethylformamide. The resulting mixture is heated at 90° C. for approximately 16 hours. At the conclusion of this period, the reaction mixture is cooled to room temperature, and 400 mL of a 10% aqueous solution of lithium chloride is added to the reaction mixture. The resulting mixture is extracted three times with ethyl acetate. The combined extracts are washed with 200 mL of the 10% aqueous solution of lithium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate is concentrated under reduced pressure, leaving a residue which is then passed through a column of silica gel, eluting with ethyl acetate. The product-containing fractions are combined, and the solvent is evaporated under reduced pressure, leaving methyl 2-ethoxycarbonylmethoxy-3-nitrosalicylate as a residue.

後処理

  1. customIn a flask are placed
  2. temperatureAt the conclusion of this period, the reaction mixture is cooled to room temperature
  3. extractionThe resulting mixture is extracted three times with ethyl acetate
  4. washThe combined extracts are washed with 200 mL of the 10% aqueous solution of lithium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customleaving a residue which
  9. washeluting with ethyl acetate
  10. customthe solvent is evaporated under reduced pressure

出典と根拠

ORDレコード
ord-1f4db3813d0445bf8b98cacda36330bd
出典データセット
uspto-grants-1996_05
特許番号
US05521147

反応ノート

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