홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Ethanol → Diethyl acetamide 2-(4-octanoyl phenyl)ethyl malonate

HRID 1595066
노트
인쇄 미리보기

반응식

HRID 1595066 반응식
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[CH2:8]([CH:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12])[CH3:9].[H-].[Na+].[CH:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:22][CH:21]=1)=[CH2:19].C(O)C>CN(C)C=O>[CH2:8]([CH:10]([CH2:14][CH3:15])[C:11]([NH2:13])=[O:12])[CH3:9].[C:1]([O:7][CH2:19][CH2:18][C:20]1[CH:25]=[CH:24][C:23]([C:26](=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:22][CH:21]=1)(=[O:6])[CH2:2][C:3]([O-:5])=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 125415361-(4-Ethenylphenyl)octan-1-oneHCID 22466969Diethyl acetamide malonate

생성물 1

HCID 86757349Diethyl acetamide 2-(4-octanoyl phenyl)ethyl malonate수율 78.4%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

4′-(2-Iodoethyl)octanophenone prepared (5 g) in the step D-3 was dissolved in anhydrous N,N-dimethylformamide (15 ml) to obtain 4′-(2-iodoethyl)octanophenone solution. Diethyl acetamide malonate (9.09 g) was dissolved in anhydrous N,N-dimethylformamide (30 ml) to obtain a solution to which 60% sodium hydride oil dispersion (1.23 g) was added with cooling. The solution was stirred under atmosphere of nitrogen for 1 hour. 4′-(2-Iodoethyl)octanophenone solution was added to the solution, and the solution was stirred under atmosphere of nitrogen at 60° C. for 2 hours. The reaction solution was poured into ice water, and extracted with ether, and washed with saturated saline solution. The extracted solution was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography using hexane-ethyl acetate (1:0→3:1) as an eluate to obtain diethyl acetamide-2-(4-octanoyl phenyl)ethyl malonate (3.2 g) and 4′-vinyl octanophenone (1.5 g) in the form of colorless crystal, respectively. The diethyl acetamide malonate (4.25 g) was dissolved in anhydrous N,N-dimethylformamide (30 ml) to obtain a solution, to which 60% sodium hydride oil dispersion (574 mg) was added. The solution was stirred under atmosphere of nitrogen at room temperature for 30 minutes. 4′-Vinyl octanophenone (1.5 g) and anhydrous ethanol (7.5 ml) were added to the solution, and the solution was stirred under atmosphere of nitrogen at 60° C. for 6 hours, and the solution was stirred at room temperature for 2 days. The reaction solution was poured into ice water, extracted with ether, and washed with saturated saline solution. The extracted solution was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography using hexane-ethyl acetate (1:0→4:1) as an eluate to obtain diethyl acetamide-2-(4-octanoyl phenyl)ethyl malonate (2.29 g) in the form of colorless crystal.

후처리

  1. customto obtain a solution
  2. stirringthe solution was stirred under atmosphere of nitrogen at 60° C. for 6 hours
  3. stirringthe solution was stirred at room temperature for 2 days
  4. extractionextracted with ether
  5. washwashed with saturated saline solution
  6. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c8678d29c1e14583b08a9eb4bf583347
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06284915B1

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트