Acetone → HCID 138058, compound

HRID 1876934Notes

Reaction equation

HRID 1876934 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

6

Reactant 4

HCID 180AcetoneHCID 707414-BromobenzaldehydeHCID 811292-BromobenzaldehydeHCID 145742L-Proline

Product 1

HCID 138058HCID 138058, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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%).

Sources & evidence

ORD record
ord-3c3c18118d9e41c4bb1049ccf6eeb6da
Source dataset
uspto-grants-2012_11
Patent number
US08309736B2

Reaction notes

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