Methyl iodide → 3-(3,4-Dichloro-phenyl)-3-methyl-dihydro-furan-2-one

HRID 734274Notes

Reaction equation

HRID 734274 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][CH2:12][O:11][C:10]2=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].I[CH3:18].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:18])[CH2:13][CH2:12][O:11][C:10]2=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 118064963-(3,4-Dichloro-phenyl)-dihydro-furan-2-one

Product 1

HCID 578435633-(3,4-Dichloro-phenyl)-3-methyl-dihydro-furan-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 18.5 g (80 mmol) 3-(3,4-dichloro-phenyl)-dihydro-furan-2-one, 3.84 g (88 mmol) NaH (55% suspension) and 14.2 g (100 mmol) iodomethane in 300 mL THF was stirred for 64 h at room temperature. NH4Cl aq. sat. was added and the mixture was extracted with ethyl acetate. The organic phases were washed with NaCl aq. sat. dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by flash column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane. The product containing fractions were evaporated to yield 16 g (82%) of the title compound as yellow oil. MS(m/e): 246.0 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phases were washed with NaCl aq.
  3. dry with materialsat. dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography on silica eluting with a gradient
  7. customformed from ethyl acetate and heptane
  8. additionThe product containing fractions
  9. customwere evaporated

Sources & evidence

ORD record
ord-85191ad12c4c44aa83b211b850c6b6ac
Source dataset
uspto-grants-2009_09
Patent number
US07592345B2

Reaction notes

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