Acetone → HCID 138058, compound

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.N1CCC[C@H]1C(O)=O.[CH3:18][C:19]([CH3:21])=[O:20].BrC1C=CC=CC=1C=O>CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:18][C:19](=[O:20])[CH3:21])=[CH:4][CH:3]=1

Participants

Procedure

The p-bromobenzaldehyde (1 mmol) and the L-proline (30 mol %) are dissolved in N,N′-dimethylimidazolium methyl H-phosphonate (1 ml). The acetone (1 ml) is added. The mixture is stirred at room temperature until disappearance of the bromobenzaldehyde (followed by Thin Layer Chromatography). 4-(4-bromophenyl)but-3-en-2-one is isolated by extraction with ether (3×5 ml). The product is purified by column chromatography (0.96 g; yield=80%).