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

HRID 860415노트

반응식

HRID 860415 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 57444529Ethyl 7-acetyl-7-(4-cyanobenzoyl)-8-oxononanoate수율 57.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
20 °C

실험 절차

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 (3.52 g) as an oil.

후처리

  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)

출처 및 근거

ORD 기록
ord-9f60228310a348638454aac9d84d4d3c
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153854B2

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