4-Pentynoic acid → 4-[4-(2-Oxazolin-2-yl) benzylidene]-1-(4-pentynoyl)piperidine
Reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].[O:8]1[CH2:12][CH2:11][N:10]=[C:9]1[C:13]1[CH:25]=[CH:24][C:16]([CH:17]=[C:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:15][CH:14]=1>O1CCCC1>[O:8]1[CH2:12][CH2:11][N:10]=[C:9]1[C:13]1[CH:14]=[CH:15][C:16]([CH:17]=[C:18]2[CH2:19][CH2:20][N:21]([C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[CH2:22][CH2:23]2)=[CH:24][CH:25]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
356 mg (2.2 mmol) of N,N'-carbonyldiimidazole in 3 ml of tetrahydrofuran are added to 200 mg (2 mmol) of 4-pentynoic acid in 2 ml of tetrahydrofuran at ambient temperature. The mixture is stirred at 40° C. for 1 hour. 363 mg (1.5 mmol) of 4-[4-(2-oxazolin-2-yl)benzylidene]piperidine are then added and the mixture is stirred at 40° C. for a further 2 hours. The reaction solution is then evaporated down and the residue is purified by column chromatography (Silica gel; ethyl acetate). 320 mg (66% of theory) of the title compound of melting point 118° C. are obtained.