Reaktion #966043

Reaktionsgleichung

Pyridine

N,N-dimethylaminoethanol

2-decenoic acid chloride

→

aimed compound

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

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was heated
2. 2
   Temperaturto reflux on a hot water bath for 3 hours
3. 3
   Sonstigetetrahydrofuran was evaporated in vacuo, water and ethyl acetate
4. 4
   workup.ADDITIONwere added to the residue
5. 5
   Sonstigeto partition
6. 6
   Sonstigean ethyl acetate layer was collected
7. 7
   WaschenThe ethyl acetate layer was washed with water
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeby purifying by silica gel column chromatography (developer: chloroform)

Vorschrift

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.

Quelle