Methyl iodide → HCID 25050336, compound

HRID 505851Notes

Reaction equation

HRID 505851 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:13]=[CH:14]\[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[CH:18]3)[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1.I[CH3:25]>CS(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7](/[CH:13]=[CH:14]\[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:25])[CH:19]=[CH:18]3)[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 25050333HCID 25050333, compound

Product 1

HCID 25050336HCID 25050336, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of KOH (2 mmol, 112 mg) in DMSO (5 mL) is stirred for 5 min. Then, compound 12a (1 mmol, 279 mg) and iodomethane (1.2 mmol, 75 μL) are added to the solution. The mixture is stirred at room temperature for 30 min, poured into water/ice, and extracted with ethyl acetate. The combined organic extracts are washed with brine (5 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure affords a residue, which is chromatographed on silica gel (20% ethyl acetate/light petroleum).

Workup

  1. stirringThe mixture is stirred at room temperature for 30 min
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with brine (5 mL)
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent under reduced pressure
  6. customaffords a residue, which
  7. customis chromatographed on silica gel (20% ethyl acetate/light petroleum)

Sources & evidence

ORD record
ord-8c9fa61b9a75479aaca9b2cb6e23d62b
Source dataset
uspto-grants-2010_08
Patent number
US07781580B2

Reaction notes

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