2(3H)-Benzofuranone → HCID 23302816, compound

HRID 1953293Notes

Reaction equation

HRID 1953293 reaction equation
[O:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[Cl-].[C:12]([C:14]1[CH:39]=[CH:38][C:17]([CH2:18][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:16][CH:15]=1)#[N:13].[K].CC(C)([O-])C>C1(C)C(C)=CC=CC=1>[O:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH:3]=[C:2]1[CH2:18][C:17]1[CH:38]=[CH:39][C:14]([C:12]#[N:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 683822(3H)-BenzofuranoneHCID 2724468(4-Cyanobenzyl)triphenylphosphonium chlorideHCID 50987170Potassium tertbutoxide

Product 1

HCID 23302816HCID 23302816, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10.4 g (77.3 mmol) of 2-coumaranone are dissolved in 200 ml xylene and after the addition of 32 g (77.3 mmol) of 4-cyanobenzyl-triphenylphosphonium chloride and 8.7 g (77.3 mmol) of potassium-tert.butoxide the mixture is refluxed for 3 hours under a nitrogen atmosphere. The solvent is distilled off, the residue is taken up in ethyl acetate, combined with silica gel and concentrated by evaporation. Then it is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (8:2). The desired fractions are combined and concentrated by evaporation.

Workup

  1. temperatureis refluxed for 3 hours under a nitrogen atmosphere
  2. distillationThe solvent is distilled off
  3. concentrationconcentrated by evaporation
  4. customThen it is chromatographed on silica gel
  5. washeluted with petroleum ether/ethyl acetate (8:2)
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-99f5647b92a04caab8badd043b11b7e0
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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