Methyl iodide → Ethyl 3-(2-fluorophenyl)-2-methyl-3-oxopropanoate

HRID 1618624Notes

Reaction equation

HRID 1618624 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:16]([O-])([O-])=O.[K+].[K+].IC.CC(O)=O.O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:15])[CH:9]([CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 296342Ethyl 3-(2-fluorophenyl)-3-oxopropanoateHCID 21899381Acetic acid--water (1/1)

Product 1

HCID 67285418Ethyl 3-(2-fluorophenyl)-2-methyl-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-(2-fluorophenyl)-3-oxopropanoate (4.2 g, 20 mmol) in DMF (30 mL) at 0° C. was added K2CO3 (3.87 g, 28 mmol) portionwise and the mixture was stirred for 30 minutes. After this time iodomethane (1.49 mL, 24 mmol) was added and the reaction mixture was allowed to warm to rt for 2 h. After this time the reaction was treated with 50 mL AcOH/water (5 mL AcOH/45 mL water). The mixture was extracted with EtOAc and the organic layer was washed with brine, dried over Mg2SO4, filtered and evaporated in vacuo to give ethyl 3-(2-fluorophenyl)-2-methyl-3-oxopropanoate. Observed some dimethyl product. Used as crude for the next step. Mass Spectrum (ESI) m/e=225 (M+1).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Mg2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-890c4f04a9e34dfd867c9e1cf3847890
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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