Dimethylformamide → Ethyl 7-methoxy-1-benzofuran-2-carboxylate

HRID 430784

反応式

HRID 430784 の反応式
CN(C)C=O.O=[CH:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:11]([O:12][CH3:13])[C:9]=1[OH:10].Cl[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:13][O:12][C:11]1[C:9]2[O:10][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7][C:8]=2[CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7751Ethyl chloroacetateHCID 8991o-VanillinHCID 11430Potassium Carbonate

生成物 1

HCID 521284Ethyl 7-methoxy-1-benzofuran-2-carboxylate収率 48%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To N,N-dimethylformamide (300 ml), o-vanillin (25.2 g), ethyl chloroacetate (23.5 ml) and potassium carbonate (45 mg) were added and the resulting mixture was stirred at 120° C. for 14 hours. The reaction mixture was filtered to remove insoluble inorganic salts, and 1N hydrochloric acid (50 ml) was added to the mixture to stop the reaction. Distilled water (250 ml) was added and the resulting mixture was extracted 4 times with totally 150 ml of ethyl acetate containing 15% of n-hexane. The organic layers were washed with distilled water (100 ml) and with saturated brine (100 ml), and dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration and the solvent was concentrated to dryness under reduced pressure. The residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=10/1 to 5/1) using silica gel to obtain the desired compound (17.4 g, yield: 48%) in the form of colorless needle-shaped crystals.

後処理

  1. filtrationThe reaction mixture was filtered
  2. customto remove insoluble inorganic salts, and 1N hydrochloric acid (50 ml)
  3. additionwas added to the mixture
  4. customthe reaction
  5. extractionthe resulting mixture was extracted 4 times with totally 150 ml of ethyl acetate containing 15% of n-hexane
  6. washThe organic layers were washed with distilled water (100 ml) and with saturated brine (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe sodium sulfate was removed by filtration
  9. concentrationthe solvent was concentrated to dryness under reduced pressure
  10. customThe residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=10/1 to 5/1)

出典と根拠

ORDレコード
ord-e4b60001689a4e48aa41680344af977e
出典データセット
uspto-grants-2001_11
特許番号
US06323235B1

関連ノート

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