Methyl iodide → 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-3-methoxy-cyclopent-2-enone

HRID 2170818Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:20][CH3:21])=[C:11]([CH:13]3[C:17](=[O:18])[CH2:16][CH2:15][C:14]3=[O:19])[N:12]=2)=[CH:4][CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:20][CH3:21])=[C:11]([C:13]3[C:17](=[O:18])[CH2:16][CH2:15][C:14]=3[O:19][CH3:22])[N:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-cyclopentane-1,3-dione (650 mg, 2.03 mmol) in acetone (10 ml) was added potassium carbonate (553 mg, 4 mmol), followed by iodomethane (248 μl, 4 mmol), and the reaction heated to 40° C. for 6 hours. The solvent was then removed from the crude reaction mixture under reduced pressure and the residue partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-ethyl-thiazol-4-yl]-3-methoxy-cyclopent-2-enone (395 mg).

Workup

customThe solvent was then removed from the crude
customreaction mixture under reduced pressure
customthe residue partitioned between water (100 ml) and ethyl acetate (100 ml)
customThe organic layer was separated
customdry loaded onto silica
custompurified by flash chromatography

Sources & evidence

ORD record: ord-0c5b07ee93d6400882f76786bb9f2c6e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051300B2

Reaction notes

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