ORGANIC SPECTROSCOPY INTERNATIONAL: ethyl (2Z)-2-(3-oxo-2-benzofuran-1-ylidene)acetate

ethyl (2Z)-2-(3-oxo-2-benzofuran-1-ylidene)acetate
218.2054 g/mol, C12H10O4

Ethyl (Z)-3-phthalidylideneacetate;

[3-Oxoisobenzofuran-1(3H)-ylidene]acetic acid ethyl ester;

[(Z)-3-Oxoisobenzofuran-1(3H)-ylidene]acetic acid ethyl ester;

Synthesis of ethyl 2-(3-oxo-1,3-dihydro-1-isobenzofurany liden)acetate (2) A solution of phthalic anhydride (1.0 equiv.) and ethyl 2- (1,1,1-triphenyl-5 -phosphanylidene)acetate (1.1 equiv.) in 300 ml of dichloromethane (DCM) was refluxed for 3 hr. DCM was removed by vacuum at 40-50 o C. 2×150 ml of hexane was added to the resulting sticky solid, stirred for 10 min and the un-reacted 2-(1,1,1-triphenyl-5 -phosphanylidene)acetate was removed by filtration. The organic solvent was removed under vacuum and the resulting crude semisolid was taken to next step without further purification. Yield: 84%.

1 H-NMR CDCl3; (ppm): 1.1 (t, 3H), 4.2 (q, 2H), 6.0 (s, 1H), 7.6 (t, 1H), 7.7 (t, 1H), 7.8 (d, 1H), 8.9 (d, 1H). S

Medicinal Chemistry, 2009, Vol. 5, No. 5,

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