Phenacyl bromide → Ethyl 2-cyano-4-oxo-4-phenylbutanoate

HRID 1012373ノート

反応式

HRID 1012373 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:8].[CH2:15](Br)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>CC(C)=O>[C:7]([CH:9]([CH2:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:8]

参加物

5

反応物 3

HCID 6259Phenacyl bromideHCID 7764Ethyl cyanoacetateHCID 11430Potassium Carbonate

生成物 1

HCID 15633746Ethyl 2-cyano-4-oxo-4-phenylbutanoate収率 90%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
42.5 °C

実験手順

Potassium carbonate (13.82 g) was added to ethyl cyanoacetate (37 mL), and the mixture was stirred at 40-45° C. for 45 min. A solution (100 mL) of phenacyl bromide (10.0 g) in acetone was added dropwise over 30 min. After completion of the dropwise addition, the mixture was stirred at room temperature for 18 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Excess ethyl cyanoacetate contained in the obtained oil was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1→1:1) to give the title compound as a pale-yellow oil (yield 10.41 g, 90%).

後処理

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature for 18 hr
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customwas evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=8:1→1:1)

出典と根拠

ORDレコード
ord-8195db06c8344699b9f8ab4b4f014008
出典データセット
uspto-grants-2011_07
特許番号
US07977488B2

反応ノート

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