Chlorosuccinimide → Chloro[1-(4-methoxyphenyl)cyclopropyl]acetaldehyde

Reaction equation

N1CCC[C@H]1C(O)=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2([CH2:20][CH:21]=[O:22])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[Cl:23]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Cl:23][CH:20]([C:17]1([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH2:19][CH2:18]1)[CH:21]=[O:22]

Participants

Procedure

L-Proline (10 mg, 0.1 mmol) was added to a solution of [1-(4-methoxyphenyl)cyclopropyl]acetaldehyde (100 mg, 0.53 mmol) in chloroform (1 mL) at 0° C. followed by addition of N-chlorosuccinimide (84 mg, 0.63 mmol). The reaction mixture was stirred at ambient temperature for 2 h. The mixture was diluted with hexanes and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in hexanes (0-10%) to afford the desired product.