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

HRID 1756173

反応式

HRID 1756173 の反応式
[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]

参加物

13

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-a7fb21fd540b4a189aff2996d81cc086
出典データセット
uspto-grants-1995_08
特許番号
US05439932

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