Pyridine → Ethyl 7-acetyl-7-(4-cyanobenzoyl)-8-oxononanoate

HRID 2250557ノート

反応式

HRID 2250557 の反応式
[C:1]([CH:4]([C:15](=[O:17])[CH3:16])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].[Cl-].[Mg+2].[Cl-].N1C=CC=CC=1.[C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)#[N:28]>ClCCl>[C:1]([C:4]([C:33](=[O:34])[C:32]1[CH:36]=[CH:37][C:29]([C:27]#[N:28])=[CH:30][CH:31]=1)([C:15](=[O:17])[CH3:16])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 1049PyridineHCID 801724-Cyanobenzoyl chlorideHCID 5360315Magnesium ChlorideHCID 14691968Ethyl 7-acetyl-8-oxononanoate

生成物 1

HCID 57444529Ethyl 7-acetyl-7-(4-cyanobenzoyl)-8-oxononanoate収率 5,740.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
20 °C

実験手順

To a mixture of ethyl 7-acetyl-8-oxononanoate (4.0 g) and magnesium chloride (1.27 g) in dichloromethane (70 ml) was added pyridine (2.15 ml) at 0° C. The mixture was stirred at 20° C. for 1 hour, then a solution of 4-cyanobenzoyl chloride (2.87 g) in dichloromethane (10 ml) was added. After stirring for 3 hours at 20° C., the mixture was partitioned between ether and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give ethyl 7-acetyl-7-(4-cyanobenzoyl)-8-oxononanoate (352 g) as an oil.

後処理

  1. stirringAfter stirring for 3 hours at 20° C.
  2. customthe mixture was partitioned between ether and 1N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)

出典と根拠

ORDレコード
ord-f7cd97cb465043498227ac168238cfd4
出典データセット
uspto-grants-2008_01
特許番号
US07317009B2

反応ノート

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