Potassium Iodide → Ethyl 5-(2-(4-nitrophenyl)-3-oxobutyl)-2-furancarboxylate

HRID 581037

反応式

HRID 581037 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:17][C:18]1[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:19]=1.[I-].[K+]>CN(C)C=O.C(OCC)C.O.C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:11](=[O:13])[CH3:12])[CH2:17][C:18]2[O:22][C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:19]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

参加物

9

反応物 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 2193671-(4-Nitrophenyl)propan-2-oneHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

生成物 1

HCID 15458175Ethyl 5-(2-(4-nitrophenyl)-3-oxobutyl)-2-furancarboxylate収率 98.8%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

3.00 g of p-nitrophenylacetone was dissolved in 50 ml of dimethylformamide, and 0.70 g of 60% oily sodium hydride was added under cooling with ice with stirring, followed by stirring at the same temperature for 10 minutes. 5 ml of a dimethylformamide solution containing 3.40 g of ethyl 5-chloromethyl-2-furancarboxylate, and 3.05 g of potassium iodide were added thereto, followed by stirring at room temperature for 2.5 hours. Then, the reaction solution was acidified by an addition of acetic acid. Water and ethyl ether were added, and the mixture was extracted. Then, the organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1+2/1) to obtain 5.48 g of the above-identified compound.

後処理

  1. temperatureunder cooling with ice
  2. stirringby stirring at the same temperature for 10 minutes
  3. additionwere added
  4. stirringby stirring at room temperature for 2.5 hours
  5. extractionthe mixture was extracted
  6. washThen, the organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1+2/1)

出典と根拠

ORDレコード
ord-e0df02dec7994e679ebc5914705212eb
出典データセット
uspto-grants-1999_07
特許番号
US05919786

関連ノート

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