Diethyl Ether → 1-[1-(3,4-Dichlorophenyl)cyclopentyl]ethanone
Reaction equation
C[Mg]I.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2(C#N)[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11].CC[O:21][CH2:22][CH3:23]>>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:22](=[O:21])[CH3:23])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]Participants
Procedure
Methylmagnesium iodide (3M solution in ether; 100 ml) was added dropwise at 0° C. under nitrogen to a stirred solution of 1-(3,4-dichlorophenyl)cyclopentanecarbonitrile (48 g) in ether (100 ml), then the mixture was stirred at ambient temperature for 24 hours. The resulting solid was collected by filtration, washed well with ether, and added in portions to an ice-cold mixture of water (200 ml) and concentrated hydrochloric acid (125 ml). The mixture was heated at 95° C. with occasional stirring for 1 hour, then it was allowed to cool to ambient temperature. The product was extracted into ether (5×100 ml), then the combined extracts were washed with water (2×100 ml), dried (MgSO4), and the solvent was removed in vacuo. The residue was distilled to give 1-[1-(3,4-dichlorophenyl)cyclopentyl]ethanone as a pale yellow oil (31.9 g), b.p. 124-128° C/0.5 mbar.
Workup
- filtrationThe resulting solid was collected by filtration
- washwashed well with ether
- additionadded in portions to an ice-cold mixture of water (200 ml) and concentrated hydrochloric acid (125 ml)
- temperatureThe mixture was heated at 95° C.
- stirringwith occasional stirring for 1 hour
- temperatureto cool to ambient temperature
- extractionThe product was extracted into ether (5×100 ml)
- washthe combined extracts were washed with water (2×100 ml)
- dry with materialdried (MgSO4)
- customthe solvent was removed in vacuo
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-1d1df468e30544a0bf5ccf45965204e9
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06187802B1
Reaction notes
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