Magnesium → HCID 59202233, compound

HRID 1685811Notes

Reaction equation

HRID 1685811 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][S:4][C:3]1=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.[Mg]>CO.O1CCCC1.O.C(O)(=O)C>[O:1]=[C:2]1[CH2:6][CH2:5][S:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

7

Reactant 2

HCID 5462224Magnesium2×HCID 67264968HCID 67264968, compound

Product 1

HCID 59202233HCID 59202233, compoundYield 26.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-[4-(3-Oxothiolan-2-ylidenemethyl)phenyl]propionic acid (500 mg) obtained in Example 14 was dissolved in a mixture of methanol (20 ml)/tetrahydrofuran (10.0 ml)/water (5.0 ml)/acetic acid (1.1 ml), and to the solution was added magnesium (150 mg). The mixture was stirred at room temperature for 2 hours, and then further magnesium (80 mg) was added, and further the solution was stirred for 2 hours. To the reaction mixture was added water and acetic acid, the solution was concentrated under reduced pressure. Saturated brine was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (132 mg, 26%).

Workup

  1. stirringfurther the solution was stirred for 2 hours
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionSaturated brine was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-5bf04429a7414ec5843c1a00451adc63
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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