Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → ethyl (4-amino-3-oxo-3H-isobenzofuran-1-ylidene)-acetate

HRID 2112072Notes

Reaction equation

HRID 2112072 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[O:5][C:6]2=O.[CH2:13]([O:15][C:16]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:17])[CH3:14]>O1CCCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[O:5][C:6]2=[CH:18][C:16]([O:15][CH2:13][CH3:14])=[O:17]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 3455514-Aminoisobenzofuran-1,3-dione

Product 1

HCID 86606182ethyl (4-amino-3-oxo-3H-isobenzofuran-1-ylidene)-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (3.1 mmol) 4-amino-isobenzofuran-1,3-dione and 1.13 g (3.1 mmol) (ethoxy-carbonylmethylene)-triphenylphosphorane are dissolved in 5 ml of tetrahydrofuran (THF) and refluxed for 3 h. Then the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (75:25).

Workup

  1. temperaturerefluxed for 3 h
  2. customThe crude product is purified by column chromatography
  3. additiona mixture of cyclohexane:ethyl acetate (75:25)

Sources & evidence

ORD record
ord-23c246ae473a45ec842d9bf58dd5b58d
Source dataset
uspto-grants-2009_04
Patent number
US07521457B2

Reaction notes

Loading…