Ethyl Acetate → HCID 18936412, compound

HRID 2955Notes

Reaction equation

HRID 2955 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]2[S:17][CH2:16][NH:15][C:14]2=[O:18])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])[CH3:3].[Mg].C(OCC)(=O)C>CO>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]2[S:17][CH2:16][NH:15][C:14]2=[O:18])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5462224Magnesium3×HCID 544685495-[[3-(1,1-Dimethylethyl)-4-hydroxyphenyl]methylene]-4-thiazolidinone

Product 1

HCID 18936412HCID 18936412, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A portion of the title compound from Example 77 (395.1 mg; 1.5 mmol) was dissolved in 9 ml of methanol. Magnesium (72.9 mg; 3.0 mmol) was then added to the solution and the resulting reaction mixture was stirred at room temperature for 3 hours. After 3 hours, most of the magnesium which had been added originally appeared to be gone so an additional 182.3 mg (7.5 mmol) of magnesium were added. Stirring of the reaction solution at room temperature continued overnight. By the next morning a yellow precipitate had formed. This precipitate was dissolved by adding the methanolic reaction solution to an ethyl acetate/1N hydrochloric acid mixture. The organic layer from the resulting two-phase mixture was isolated and then dried over sodium sulfate. The volatile components of the organic layer were removed and the resulting residue was chased with methylene chloride. The residue was then dissolved in 25 ml of methylene chloride and the resulting solution was chromatographed on a silica gel chromatography column using a 5-20% isopropyl alcohol in hexanes gradient. Those fractions identified as containing essentially pure product were evaporated to provide 0.29 g of title compound. m.p. 65°-70° C.

Workup

  1. customthe resulting reaction mixture
  2. waitAfter 3 hours
  3. additionwere added
  4. stirringStirring of the reaction solution at room temperature
  5. waitcontinued overnight
  6. customBy the next morning a yellow precipitate had formed
  7. dissolutionThis precipitate was dissolved
  8. customThe organic layer from the resulting two-phase mixture was isolated
  9. dry with materialdried over sodium sulfate
  10. customThe volatile components of the organic layer were removed
  11. dissolutionThe residue was then dissolved in 25 ml of methylene chloride
  12. customthe resulting solution was chromatographed on a silica gel chromatography column
  13. additionas containing essentially pure product
  14. customwere evaporated

Sources & evidence

ORD record
ord-da305453c99c4c2c9addcfb5438c3fa0
Source dataset
uspto-grants-1998_03
Patent number
US05731336

Reaction notes

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