Hydrochloric Acid → HCID 15017666, compound

HRID 1682260Notes

Reaction equation

HRID 1682260 reaction equation
[CH:1]([C:3]1[C:4]([F:14])=[C:5]([CH:9]=[C:10]([F:13])[C:11]=1[F:12])[C:6]([OH:8])=O)=[CH2:2].[C:15]([C:22]1NC=CN=1)(C1NC=CN=1)=[O:16].C([CH:29](C([O-])=O)[C:30]([O-])=[O:31])C.C(C(C([O-])=O)C([O-])=O)C.[Mg+2].[Mg+2].Cl>C1COCC1>[CH:1]([C:3]1[C:4]([F:14])=[C:5]([C:6](=[O:8])[CH2:29][C:30]([O:16][CH2:15][CH3:22])=[O:31])[CH:9]=[C:10]([F:13])[C:11]=1[F:12])=[CH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 15017665HCID 15017665, compoundHCID 19046054HCID 19046054, compound

Product 1

HCID 15017666HCID 15017666, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (0° to 5° C.) of 3-ethenyl -2,4,5-trifluorobenzoic acid (6.0 g, 0.03 mol) in THF (100 mL) was added carbonyl diimidazole (4.9 g, 0.030 mol). The mixture was then stirred at room temperature for 1 hour, heated with magnesium bis(ethyl malonate) (8.7 g, 0.03 mol) and refluxed for 3 hours. The reaction was allowed to cool, treated with 3 N HCl (30 mL) and stirred for 1.5 hours at room temperature. The reaction was partitioned between ether and water. The organic layer was dried and concentrated to provide 7.65 g (93%) of the desired product. An analytical sample was obtained by preparative TLC (SiO2, 9:1 hexane/EtOAC)

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureto cool
  3. stirringstirred for 1.5 hours at room temperature
  4. customThe reaction was partitioned between ether and water
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e777f2424fff463c94e30ff9e5e0a218
Source dataset
uspto-grants-1992_12
Patent number
US05175356

Reaction notes

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