Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 23084554, compound

HRID 2111622Notes

Reaction equation

HRID 2111622 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH:5]2O.[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH:5]2[CH2:26][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 23084546HCID 23084546, compound

Product 1

HCID 23084554HCID 23084554, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product of above-mentioned (1-b) (0.90 g, 3.3 mmol) and (carboethoxymethylene)triphenylphosphorane (1.4 g, 3.9 mmol) was heated under reflux in toluene (15 ml) under an argon atmosphere for 3.5 hrs. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform methanol=50:1) to give 0.37 g of 5,6-dimethyl-2-(4-fluorophenyl)-3-ethoxycarbonylmethylisoindolin-1-one [IUPAC name: ethyl 2-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetate].

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (chloroform methanol=50:1)

Sources & evidence

ORD record
ord-273dff4f54924c1b9dbac91f32e2a57d
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

Loading…