3-(4-Chlorophenoxy)pyrrolidine → 1-[3-(4-Chlorophenoxy)-1-pyrrolidinyl]-3-(3,5-difluoro-2-nitrophenoxy)-2-propanol
Reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]2[CH2:11][CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.[F:14][C:15]1[C:16]([N+:27]([O-:29])=[O:28])=[C:17]([CH:23]=[C:24]([F:26])[CH:25]=1)[O:18][CH2:19][CH:20]1[CH2:22][O:21]1>C(O)C>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH:7]2[CH2:11][CH2:10][N:9]([CH2:22][CH:20]([OH:21])[CH2:19][O:18][C:17]3[CH:23]=[C:24]([F:26])[CH:25]=[C:15]([F:14])[C:16]=3[N+:27]([O-:29])=[O:28])[CH2:8]2)=[CH:4][CH:3]=1Participants
4
Procedure
A solution of 3-(4-chlorophenoxy)pyrrolidine and 2-[(3,5-difluoro-2-nitrophenoxy)methyl]oxirane (50 mg, 0.216 mmol) in ethanol was refluxed for 3 hrs. The solvent was distilled off under reduced pressure and the resulting residue purified by silica gel column chromatography (dichloromethane/methanol 20:1) to give 45 mg (0.105 mmol) of the title compound as solid.