Acrolein → (E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine

HRID 1756173

반응식

HRID 1756173 반응식
[CH2:1]([NH:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH:11]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28]/[CH:29]=[CH:30]/[C:31]#[C:32][Si:33]([CH3:36])([CH3:35])[CH3:34].OC(C=C)C#C[Si](C)(C)C.C[Si](C#C)(C)C.C(C=C)=O.CS(Cl)(=O)=O.[Br-].C[NH+](C)C>CN(C)C=O.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([N:3]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH:11]=1)[CH2:28]/[CH:29]=[CH:30]/[C:31]#[C:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:2]

참가 물질

13

반응물 8

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66111TrimethylsilylacetyleneHCID 10954986(5-Bromopent-3-en-1-yn-1-yl)trimethylsilaneHCID 14544808Trimethyl ammonium bromideHCID 199170335-(Trimethylsilyl)pent-1-en-4-yn-3-olHCID 19917042N-ethyl-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine

생성물 1

HCID 19917013(E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine수율 82.5%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

1.9 g of N-ethyl-2-[2-[3-(3-thienyl)phenoxy]-ethoxy]ethylamine and 2.7 g of potassium carbonate were dissolved in 15 ml of dimethylformamide, and a dimethylformamide solution (5 ml) of 1.43 g of (E)-5-bromo-3-penten-1-ynyl(trimethyl)silane [synthesized by mesylating 3-hydroxy-4-penten-1-ynyl(trimethyl)silane, prepared from trimethylsilylacetylene and acrolein, with methanesulfonyl chloride and triethylamine, and subsequently treating the mesylated product with trimethylammonium bromide) was added dropwise. The mixture was stirred at room temperature for 30 minutes, and then ethyl acetate and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [methylene chloride/methanol=20/1] to give 2.3 g of (E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine as a colorless oil.

후처리

  1. additionwas added dropwise
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [methylene chloride/methanol=20/1]

출처 및 근거

ORD 기록
ord-a7fb21fd540b4a189aff2996d81cc086
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05439932

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