Sodium Sulfite → Methyl 3-(2,4-dimethoxy-5-fluorophenyl)octanoate

HRID 1637534Notes

Reaction equation

HRID 1637534 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12][C:13]([O:15][CH3:16])=[O:14].[F:22][N+]1C=C(C(F)(F)F)C=CC=1S([O-])(=O)=O.S([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([F:22])=[CH:5][C:4]=1[CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 27376181-Fluoro-5-(trifluoromethyl)pyridin-1-ium-2-sulfonateHCID 19348674HCID 19348674, compound

Product 1

HCID 19348552Methyl 3-(2,4-dimethoxy-5-fluorophenyl)octanoateYield 18%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of 943 mg (3.20 mmol) of methyl 3-(2,4-dimethoxyphenyl)octanoate [prepared as described in Preparation 32(i)] in 5 ml of 1,2-dichloroethane was added to a suspension of 864 mg (3.53 mmol) of 1-fluoro-5-trifluoromethylpyridinium-2-sulfonate in 10 ml of 1,2-dichloroethane, and the resulting mixture was stirred at 90° C. for 2.5 hours. The reaction mixture was then poured into a saturated aqueous solution of sodium sulfite, and the aqueous mixture was freed from the solvent by evaporation under reduced pressure, after which it was extracted with ethyl acetate. The extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 20 g of silica gel, using an 8:1 by volume mixture of hexane and ethyl acetate as the eluent, to give a mixture containing the title compound. This mixture was further purified by column chromatography through 40 g of silica gel, using a 7:1 by volume mixture of hexane and acetone as the eluent, to give the desired fluoride compound as an oily substance in a 18% yield.

Workup

  1. customthe aqueous mixture was freed from the solvent by evaporation under reduced pressure
  2. extractionafter which it was extracted with ethyl acetate
  3. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialafter which it was dried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through 20 g of silica gel
  7. additionby volume mixture of hexane and ethyl acetate as the eluent
  8. customto give a mixture

Sources & evidence

ORD record
ord-92634ed8fa5d49e9add86b520b47fd64
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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