Pyridine → (E)-2-(dimethylamino)ethyl dec-2-enoate

HRID 878861

反応式

HRID 878861 の反応式
N1C=CC=CC=1.[CH3:7][N:8]([CH2:10][CH2:11][OH:12])[CH3:9].[C:13](Cl)(=[O:23])[CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O1CCCC1>[C:13]([O:12][CH2:11][CH2:10][N:8]([CH3:9])[CH3:7])(=[O:23])/[CH:14]=[CH:15]/[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

5

反応物 3

HCID 1049PyridineHCID 79022-(Dimethylamino)ethanolHCID 54152666Decenoyl chloride

生成物 1

HCID 56963173(E)-2-(dimethylamino)ethyl dec-2-enoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Thionyl chloride (8 ml) was added to trans-2-decenoic acid (3.4 g, 0.02 mol) followed by refluxing on a hot water bath for 2 hours. An excessive thionyl chloride was evaporated in vacuo to give 2-decenoic acid chloride. Pyridine (1 ml) was added to a solution of N,N-dimethylaminoethanol (2.0 g, 0.022 mol) in tetrahydrofuran (30 ml) followed by dropping into a solution of 2-decenoic acid chloride in tetrahydrofuran (20 ml). The reaction solution was heated to reflux on a hot water bath for 3 hours, tetrahydrofuran was evaporated in vacuo, water and ethyl acetate were added to the residue to partition and an ethyl acetate layer was collected therefrom. The ethyl acetate layer was washed with water and evaporated followed by purifying by silica gel column chromatography (developer: chloroform) to give the aimed compound as a light brown oily product.

後処理

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux on a hot water bath for 3 hours
  3. customtetrahydrofuran was evaporated in vacuo, water and ethyl acetate
  4. additionwere added to the residue
  5. customto partition
  6. customan ethyl acetate layer was collected
  7. washThe ethyl acetate layer was washed with water
  8. customevaporated
  9. customby purifying by silica gel column chromatography (developer: chloroform)

出典と根拠

ORDレコード
ord-a5503478305a4db5ae8fdf80a340d0e0
出典データセット
uspto-grants-2015_03
特許番号
US08987486B2

関連ノート

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