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

HRID 2170809Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-cyclopentane-1,3-dione (1.12 g, 3.66 mmol) in acetone (20 ml) was added potassium carbonate (1.04 g, 7.32 mmol), followed by iodomethane (455 μl, 7.32 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-methyl-thiazol-4-yl]-3-methoxy-cyclopent-2-enone (780 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-57f67a43ca4a4490b21ee6f79332735c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051300B2

Reaction notes

Loading…