Acetic Acid → HCID 20513444, compound

Reaction equation

C([C:3]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:27])[C:15]=1OC)([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:4]([O:6]CC)=[O:5])#N.I.C(O)(=O)C>O>[CH2:9]([CH:3]1[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])[C:15]=2[O:5][C:4]1=[O:6])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

Procedure

A mixture of ethyl 2-cyano-2-[2-methoxy-3-(o-tolyloxy)phenyl]-n-heptanoate (5.9 g), hydriodic acid (58%, 10 ml) and acetic acid (20 ml) was refluxed under heating for 48 hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with aqueous sodium hydrogen sulfite and water in turn, dried and evaporated under reduced pressure. To the oily residue was added acetic anhydride (5 ml), and the mixture was refluxed under heating for 10 minutes and then evaporated under reduced pressure. The resultant oily residue was purified by column chromatography (silica gel 80 g, benzene) to give oily 3-(n-pentyl)-7-(o-tolyloxy)-2,3-dihydrobenzofuran-2-one (2.5 g).