Methyl iodide → HCID 57799915, compound

HRID 2100648Notes

Reaction equation

HRID 2100648 reaction equation
CN([CH2:4][CH:5]([CH:16]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1[CH3:36])[C:17](=[CH2:28])[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)=[O:19])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)=[O:7])C.C(N(C(C)C)CC)(C)C.IC.[OH-].[K+]>C(#N)C>[F:35][C:31]1[C:30]([CH3:36])=[C:29]([CH:16]([C:17](=[CH2:28])[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=2)=[O:19])[C:5](=[CH2:4])[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[O:7])[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 57799945HCID 57799945, compound

Product 1

HCID 57799915HCID 57799915, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of crude 2-((dimethylamino)methyl)-3-(3-fluoro-2-methylphenyl)-1,5-bis(3-methoxyphenyl)-4-methylenepentane-1,5-dione (91 g, 186 mmol) in acetonitrile (769 mL) was added diisopropylethylamine (65 mL, 376 mmol) followed by iodomethane (140 mL, 2.24 mol). The mixture was stirred at room temperature for 16 h. To this mixture was added 2 M KOH (307 mL, 614 mmol), and the temperature was raised to 75° C. for 16 h. The mixture was partitioned between dichloromethane and water. The layers were separated and the aqueous phase extracted with 500 mL dichloromethane. The combined organic layers were dried over MgSO4, filtered, and evaporated to dryness. The residue was treated with 350 mL ether, isolated by filtration, and washed with 2×100 mL of ether. The ether layers were concentrated in vacuum to give 3-(3-fluoro-2-methylphenyl)-1,5-bis(3-methoxyphenyl)-2,4-dimethylenepentane-1,5-dione (63.8 g, 77% yield), (characterized by LCMS and 1H NMR). LRMS (M+H+) m/z=445.3.

Workup

  1. temperaturethe temperature was raised to 75° C. for 16 h
  2. customThe mixture was partitioned between dichloromethane and water
  3. customThe layers were separated
  4. extractionthe aqueous phase extracted with 500 mL dichloromethane
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additionThe residue was treated with 350 mL ether
  9. customisolated by filtration
  10. washwashed with 2×100 mL of ether
  11. concentrationThe ether layers were concentrated in vacuum

Sources & evidence

ORD record
ord-499f344b7fec4c908a5f68ec05031040
Source dataset
uspto-grants-2009_08
Patent number
US07572814B2

Reaction notes

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