Pyruvic Acid → Potassium 2-oxo-8-phenyl-3,5,7-octatrienoate

HRID 601085ノート

反応式

HRID 601085 の反応式
[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([OH:18])(=[O:17])[C:14]([CH3:16])=[O:15].[OH-].[K+:20]>CO>[O:15]=[C:14]([CH:16]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:13]([O-:18])=[O:17].[K+:20]

参加物

5

反応物 3

HCID 1060Pyruvic AcidHCID 14797Potassium Hydroxide2 回HCID 1146512,4-Pentadienal, 5-phenyl-

生成物 1

HCID 74088932Potassium 2-oxo-8-phenyl-3,5,7-octatrienoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
2.5 °C

実験手順

A solution of 5-phenyl-2,4-pentadienal (6.70 g) and pyruvic acid (3.0 mL) in 5 mL of methanol was stirred and chilled to 0-5° C. in an ice bath. To the chilled solution was added a solution of 35 mL of potassium hydroxide (3.5 g) in 10 mL of methanol dropwise over a period of 30 minutes. The remaining methanolic potassium hydroxide was added rapidly and the ice bath was removed. The reaction was allowed to warm to room temperature and stirred for another hour. The flask was then refrigerated overnight. The solid was collected by filtration, washed with 15 mL of methanol three times, 15 mL of ether and then air dried to afford 6.69 g of potassium 2-oxo-8-phenyl-3,5,7-octatrienoate as a yellow solid. 1H NMR (DMSO-d6, 300 MHz), δ (ppm) 7.52 (d, 2H), 7.32 (m, 3H), 7.10 (m, 2H), 6.83 (dd, 2H), 6.57 (dd, 1H), 6.13 (d, 1H).

後処理

  1. customthe ice bath was removed
  2. temperatureto warm to room temperature
  3. customrefrigerated overnight
  4. filtrationThe solid was collected by filtration
  5. washwashed with 15 mL of methanol three times, 15 mL of ether
  6. customair dried

出典と根拠

ORDレコード
ord-521f270cedee461581eef88507702ba8
出典データセット
uspto-grants-2011_03
特許番号
US07902259B2

反応ノート

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