Methyl iodide → HCID 89768310, compound

HRID 591544Notes

Reaction equation

HRID 591544 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[CH:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:8]=2[CH:7]=1.[H-].[Na+].I[CH3:27]>CN(C=O)C>[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]2[C:10]([CH3:27])([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89767875HCID 89767875, compound

Product 1

HCID 89768310HCID 89768310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-carboxylate (150 mg) in DMF (dry) (3.0 mL) was added sodium hydride (18.7 mg) at 0° C. After 30 min, to the mixture was added iodomethane (0.034 mL) at 0° C. The mixture was allowed to room temperature and stirred at room temperature overnight. The mixture was quenched with water at 0° C. and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (103.8 mg).

Workup

  1. customwas allowed to room temperature
  2. customThe mixture was quenched with water at 0° C.
  3. extractionextracted with EtOAc
  4. washThe combined organic layer was washed successively with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-b4013b2fab6445cb95c30debf1df5add
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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