HCID 22258810, compound → HCID 22258826, compound

HRID 1611129Notes

Reaction equation

HRID 1611129 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:3]=1[C:4](N(OC)C)=[O:5].[CH3:24][Mg]Br>O1CCCC1>[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[C:3]=1[C:4](=[O:5])[CH3:24]

Participants

4

Reactant 2

HCID 22258810HCID 22258810, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22258826HCID 22258826, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of 2-fluoro-N-methoxy-6-[(4-methoxybenzyl)oxy]-N-methylbenzamide (6.926 g, 21.70 mmol) in tetrahydrofuran (10 mL) was added 1N methyl magnesium bromide in tetrahydrofuran (43.40 mL, 43.40 mmol). The reaction mixture was stirred at reflux for 4 hrs. After cooled to room temperature, the reaction mixture was quenched with saturated aqueous NaHCO3 solution, and extracted with ethyl acetate. The separated organic phase was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexane:ethyl acetate, 3/1) to give 1-{2-fluoro-6-[(4-methoxybenzyl)oxy]phenyl}ethanone as a pale yellow solid (1.21 g, yield; 20%). [Starting Compound 1J]

Workup

  1. temperatureat reflux for 4 hrs
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. washThe separated organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography on silica gel (hexane:ethyl acetate, 3/1)

Sources & evidence

ORD record
ord-7a65602c2ef543bc9d9d63ceaf125049
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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