3,4,5,6-Tetrahydrophthalic anhydride → Methyl (2E)-2-(4,5,6,7-tetrahydro-3-oxo-1(3H)-isobenzofuranylidene)acetate

HRID 749100Notes

Reaction equation

HRID 749100 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.[CH3:12][O:13][C:14](=[O:35])[CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:12][O:13][C:14](=[O:35])/[CH:15]=[C:4]1/[O:6][C:1](=[O:11])[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]/1=2

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 66966450Methyl (2E)-2-(4,5,6,7-tetrahydro-3-oxo-1(3H)-isobenzofuranylidene)acetateYield 46.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3,4,5,6-tetrahydrophthalic acid anhydride (3.04 g) and (triphenylphosphoranylidene)acetic acid methyl ester (6.69 g) in chloroform (50.0 mL) was refluxed for 3 hours. After cooling the reaction mixture to room temperature, it was concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9→3:7) to give the title compound (1.93 g) having the following physical data.

Workup

  1. concentrationit was concentrated
  2. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9→3:7)

Sources & evidence

ORD record
ord-a5a242d57b4d4dc7b996d7f173fbccca
Source dataset
uspto-grants-2008_07
Patent number
US07402580B2

Reaction notes

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