Dimethylformamide → (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[3-(1-pyrrolyl)benzyloxy)benzylamine

HRID 2254406노트

반응식

HRID 2254406 반응식
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)[CH2:9][CH3:10].[H-].[Na+].CN(C)C=O.CS(O[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([N:40]2[CH:44]=[CH:43][CH:42]=[CH:41]2)[CH:35]=1)(=O)=O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:20][C:2]([CH3:19])([CH3:1])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([N:40]3[CH:44]=[CH:43][CH:42]=[CH:41]3)[CH:35]=2)[CH:13]=1)[CH2:9][CH3:10]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10445905(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamineHCID 197445313-(1-Pyrrolyl)benzyl methanesulfonate

생성물 1

HCID 19744667(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[3-(1-pyrrolyl)benzyloxy)benzylamine수율 70%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

실험 절차

100 mg of (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-hydroxybenzylamine was dissolved in 1 ml of anhydrous tetrahydrofuran, and 20 mg of 60% oily sodium hydride was added to the solution with ice cooling and stirring, and the mixture was stirred for 10 minutes. To the resulting solution was added 1 ml of a dimethylformamide solution of 100 mg of 3-(1-pyrrolyl)benzyl methanesulfonate, and the mixture was stirred overnight at room temperature. The solution was extracted by adding 20 ml of water and 30 ml of ethyl ether. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was evaporated. The residue was purified by silica gel column chromatography [Wakogel C-200, 20 g, eluting solvent: hexane/ethyl acetate=10/1→5/1) to give 110 mg (yield 70%) of the captioned compound as a colorless oil.

후처리

  1. stirringthe mixture was stirred for 10 minutes
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionThe solution was extracted
  4. additionby adding 20 ml of water and 30 ml of ethyl ether
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography [Wakogel C-200, 20 g
  10. washeluting solvent

출처 및 근거

ORD 기록
ord-8d9fce2a118849eab547964d93de47e9
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05234946

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