Methyl iodide → HCID 66926146, compound

HRID 2170823Notes

Reaction equation

HRID 2170823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([CH:14]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]3=[O:20])[CH:9]=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:12][C:11]([CH3:13])=[C:10]([C:14]3[C:15](=[O:20])[CH2:16][CH2:17][C:18]=3[O:19][CH3:21])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66926088HCID 66926088, compound

Product 1

HCID 66926146HCID 66926146, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-cyclopentane-1,3-dione (2.21 g, 7.25 mmol) in acetone (50 ml) was added potassium carbonate (1514 g, 10.87 mmol) followed by iodomethane (670 μl, 10.87 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-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-cyclopent-2-enone (818 mg).

Workup

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

Sources & evidence

ORD record
ord-cd39bc4a20e8417b9e12428f3dbe3d0b
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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