HCID 59627705, compound → HCID 59627702, compound

HRID 1930115Notes

Reaction equation

HRID 1930115 reaction equation
Cl[CH:2]([C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH3:16])=[CH:10][C:9]=1[CH3:17])[C:3]([O:5][CH2:6][CH3:7])=[O:4]>CC(O)=O.CCOC(C)=O.[Fe]>[Cl:14][C:12]1[C:11]([O:15][CH3:16])=[CH:10][C:9]([CH3:17])=[C:8]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=1

Participants

5

Reactant 1

HCID 59627705HCID 59627705, compound2×

Product 1

HCID 59627702HCID 59627702, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Iron powder (193 mg, 3.46 mmol) was added to a stirred solution of ethyl 2-chloro-2-(5-chloro-4-methoxy-2-methylphenyl)acetate (Intermediate 3-5; 480 mg, 1.73 mmol) in AcOH (2 mL) under nitrogen, and the resulting mixture was stirred at 60° C. for 17 hours. The reaction mixture was allowed to cool to ambient temperature, diluted with EtOAc (50 mL), filtered through celite and washed with saturated brine (3×25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)acetate (190 mg, 45.2%) as a colourless gum.

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through celite
  3. washwashed with saturated brine (3×25 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
  9. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-6034b41ae6a9429390eec7c7bfc9f63b
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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