Hydrochloric Acid → HCID 131721093, compound

HRID 343766Notes

Reaction equation

HRID 343766 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].C([CH:17]([C-:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1)[C:18]([O:20][CH2:21]C)=O)C.[CH-:28]1[CH:32]=[CH:31][CH:30]=[CH:29]1.[Fe+2:33].Cl>CCOCC>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]([C:27]2[CH:23]=[CH:17][C:18]([O:20][CH3:21])=[CH:25][CH:26]=2)=[C:11]([C-:28]2[CH:32]=[CH:31][CH:30]=[CH:29]2)[CH2:12][CH3:13])=[CH:3][CH:4]=1.[CH-:23]1[CH:27]=[CH:26][CH:25]=[CH:24]1.[Fe+2:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 696764-IodoanisoleHCID 178418339ButyllithiumHCID 178471213HCID 178471213, compound

Product 1

HCID 131721093HCID 131721093, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

1.20 g (5.5 mmol) of 4-iodoanisole are dissolved in 20 ml of anhydrous ether under an argon atmosphere. The solution is cooled to 0° C. and then 2.9 ml (4.6 mmol) of a 1.6M n-butyllithium solution are added dropwise. After complete addition, the mixture is maintained at 0° C. for 15 minutes. A solution of ethyl 2-ethyl-2-ferrocenylacetate (0.69 g, 2.3 mmol) dissolved in 10 ml of anhydrous ether is placed in the dropping funnel. The latter solution is added dropwise to the first solution, the temperature being maintained at 0° C. Stirring is maintained for 30 minutes at 0° C. and 2 hours at room temperature. A 1N hydrochloric acid solution is then added to a pH of 1 and the reaction mixture is heated at reflux for 4 hours. After cooling, the product is extracted with ether. The ethereal phase is first washed with water, dried over magnesium sulfate, filtered and then evaporated. The crude product obtained is chromatographed on 60GF254 silica gel plates with a 1/9 ether/pentane mixture as eluent. 0.65 g of the desired compound is obtained (Rf =0.45) with a yield of 62.5%.

Workup

  1. additionAfter complete addition
  2. temperaturethe mixture is maintained at 0° C. for 15 minutes
  3. additionThe latter solution is added dropwise to the first solution
  4. temperaturethe temperature being maintained at 0° C
  5. temperatureis maintained for 30 minutes at 0° C. and 2 hours at room temperature
  6. temperaturethe reaction mixture is heated
  7. temperatureat reflux for 4 hours
  8. temperatureAfter cooling
  9. extractionthe product is extracted with ether
  10. washThe ethereal phase is first washed with water
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customevaporated
  14. customThe crude product obtained
  15. customis chromatographed on 60GF254 silica gel plates with a 1/9 ether/pentane mixture as eluent

Sources & evidence

ORD record
ord-a9d08aea09244674b634b6e6f922824c
Source dataset
uspto-grants-1999_01
Patent number
US05863911

Reaction notes

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