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Methyl iodide → HCID 23116231, 화합물

HRID 499886
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HRID 499886 반응식
[CH2:1]([O:4][C:5]1[C:6]([CH2:38][CH3:39])=[C:7]([CH2:27][C:28]([N:30]([CH2:35][CH2:36][OH:37])[CH2:31][CH2:32][O:33][CH3:34])=[O:29])[C:8]([C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].[H-].[Na+].[CH3:42]I.[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:4][C:5]1[C:6]([CH2:38][CH3:39])=[C:7]([CH2:27][C:28]([N:30]([CH2:35][CH2:36][O:37][CH3:42])[CH2:31][CH2:32][O:33][CH3:34])=[O:29])[C:8]([C:15](=[O:26])[C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:20][CH:21]=2)=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23116349HCID 23116349, 화합물

생성물 1

HCID 23116231HCID 23116231, 화합물수율 21.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-[3,5-Diallyloxy-2-ethyl-6-(4-methanesulfonyl-benzoyl)phenyl]-N-(2-hydroxyethyl)-N-(2-methoxyethyl)-acetamide (450 mg, 0.76 mmol) obtained in Example 96, Step 1 was dissolved in N,N-dimethylformamide (10 mL), and a 60% sodium hydride dispersion in mineral oil (50 mg, 1.3 mmol) was added thereto in an atmosphere of argon with stirring under ice-cooling. The reaction mixture was stirred at room temperature for 30 minutes, and methyl iodide (0.05 mL, 0.8 mmol) was added dropwise thereto, followed by further stirring for 12 hours. After the reaction mixture was ice-cooled, a saturated aqueous solution of ammonium chloride was added thereto to stop the reaction, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1) to obtain 2-[3,5-diallyloxy-2-ethyl-6-(4-methanesulfonylbenzoyl)-phenyl]-N,N-bis(2-methoxyethyl)acetamide (95 mg, 21%).

후처리

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  3. stirringby further stirring for 12 hours
  4. temperaturecooled
  5. customthe reaction
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1)

출처 및 근거

ORD 기록
ord-fc8139e28fc84d508350d5afdb1eeefd
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07767693B2

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