Methyl iodide → HCID 58481590, compound

HRID 509169Notes

Reaction equation

HRID 509169 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2=[O:15])=[C:4]([CH3:16])[CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([C:9]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]=2[O:15][CH3:17])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58481541HCID 58481541, compound

Product 1

HCID 58481590HCID 58481590, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
27.5 °C

Procedure

To a solution of 2-(4-fluoro-2,6-dimethylphenyl)-cyclopentane-1,3-dione (2.9 g, 13.3 mmol) in tetrahydrofuran (290 ml) is added anhydrous potassium carbonate (22 g, 159 mmol) and iodomethane (22.6 g, 159 mmol. The resulting mixture is stirred at 25-30° C. for 16 hours. The organic layer is evaporated, reaction mixture is quenched with water (150 ml) and extracted with ethylacetate (3×100 ml). The combined organic extracts are combined, washed with water and brine, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(4-fluoro-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone (2 g).

Workup

  1. customThe organic layer is evaporated
  2. customreaction mixture
  3. customis quenched with water (150 ml)
  4. extractionextracted with ethylacetate (3×100 ml)
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated in vacuo
  9. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cf29d55cf6544438b5f4eabba98843b0
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

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