Ethyl Acetate → Methyl 5-chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanoate

HRID 406364Notes

Reaction equation

HRID 406364 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[Cl:17][CH2:18][CH2:19][CH2:20]I.[H-].[Na+].C(OCC)(=O)C>O1CCCC1>[Cl:17][CH2:18][CH2:19][CH2:20][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:13]([F:14])([F:15])[F:16])[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 861160344-Chloro-2-(trifluoromethyl)phenylacetic acid methyl ester

Product 1

HCID 66618825Methyl 5-chloro-2-(4-chloro-2-trifluoromethylphenyl)pentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl (4-chloro-2-trifluoromethylphenyl)acetate (5.5 g) and 3-chloro-1-iodopropane (4.6 mL) in tetrahydrofuran (15 mL) was added dropwise to a suspension of sodium hydride (containing 60% in mineral oil, 955 mg) in tetrahydrofuran (50 mL) under ice-cooling. The reaction solution was stirred at the same temperature for 10 minutes and then at room temperature for three hours and 20 minutes. Ice water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The aqueous layer was reextracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate=19:1) to obtain 5.30 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. waitat room temperature for three hours
  3. custom20 minutes
  4. customthe organic layer was separated
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (carrier: Wakogel™ C-200; elution solvent:heptane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-874548fe969f473e91e91c0a30e22fba
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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