Sodium Chloride → 4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

HRID 359635

反応式

HRID 359635 の反応式
C([O:4][CH2:5][CH2:6][N:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)[CH2:8][CH3:9])(=O)C.[Br-].[O:19]1CCO[CH:20]1[CH2:24][P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+].[Cl-].[Na+]>CN(C)C=O.Cl.O>[OH:4][CH2:5][CH2:6][N:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:24][CH:20]=[O:19])=[CH:16][CH:17]=1)[CH2:8][CH3:9]

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-HCID 22292430Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium BromideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 544515964-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of 235.3 g (1 mole) of 4-(N-2-acetoxyethyl-N-ethylamino)benzaldehyde in dimethylformamide is added 738.7 g (2.0 moles) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (224.4 g, 2.0 moles) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the solution is poured into a seven-fold excess of water, the aqueous mixture is saturated with sodium chloride, and the solution is extracted with three portions of ether. The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are dried over 4A sieves, filtered through cotton, and evaporated to yield the cinnamaldehyde as an oil. The product is purified by flash chromatography (silica gel, 1:1 hexane:ethyl acetate).

後処理

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. extractionthe solution is extracted with three portions of ether
  4. dry with materialThe combined organics are dried over 4A sieves
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customThe crude reaction product
  8. extractionAfter neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
  9. dry with materialthe combined organics are dried over 4A sieves
  10. filtrationfiltered through cotton
  11. customevaporated

出典と根拠

ORDレコード
ord-86fa6da997994c81b205357250765256
出典データセット
uspto-grants-1991_03
特許番号
US05002361

関連ノート

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