Toluene → HCID 57528562, compound

HRID 1453637Notes

Reaction equation

HRID 1453637 reaction equation
[N:1]12[CH2:8][C:5]([C:9](=[O:30])[CH:10]=P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.C1(C)C=CC=CC=1.[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH:39]=O>C(Cl)(Cl)Cl>[N:1]12[CH2:8][C:5]([C:9](=[O:30])/[CH:10]=[CH:39]/[C:38]([O:42][CH2:43][CH3:44])=[O:41])([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 70211Ethyl oxoacetateHCID 15663625HCID 15663625, compound

Product 1

HCID 57528562HCID 57528562, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.00 g (12.09 mmol) of 1-(1-azabicyclo[3.2.1]oct-5-yl)-2-(triphenylphosphanylidene)-ethanone in solution in 20 ml of chloroform and 20 ml of toluene are introduced into a 100 ml three-necked round-bottomed flask. 1.36 g (13.3 mmol) of ethyl glyoxylate are subsequently added and the reaction medium is refluxed at ambient temperature for 15 min. The solvent is eliminated by evaporation under reduced pressure and the residue obtained is purified by silica gel column chromatography, elution being carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 89/2/0.2. 1.44 g of product are obtained in the form of an amorphous solid.

Workup

  1. customThe solvent is eliminated by evaporation under reduced pressure
  2. customthe residue obtained
  3. customis purified by silica gel column chromatography, elution
  4. additionbeing carried out with a mixture of chloroform, methanol and aqueous ammonia in the proportions 89/2/0.2

Sources & evidence

ORD record
ord-a72698648ec4460e8a1ac62f550f8609
Source dataset
uspto-grants-2009_01
Patent number
US07476674B2

Reaction notes

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