1(3H)-Isobenzofuranone, 3-bromo- → 1-Ethyl-1,3,4,9-tetrahydro-7-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic Acid 3-Oxo-1-isobenzofuranyl Ester

Participants

Reaction Steps

A solution of 1-ethyl-1,3,4,9-tetrahydro-7-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic acid (0.650 g, 1.89 mmol, prepared according to the procedure of Example 1), 3-bromophthalid (0.402 g, 1.89 mmol) and TEA (0.382 g, 3.79 mmol) in dry THF (60 mL) was refluxed for 4 hours. The solvent was evaporated and the residue was partitioned between water and ether. The extracts were washed with 5% NaHCO3 and brine, dried (MgSO4) and evaporated to dryness. Flash chromatography of the residue (on silica Merck-60, eluant: CHCl3) provided 0.670 g (74.6%) of the pure product (as a mixture of diastereomers) which was recrystallized from ether-hexane, m.p. 150° C. (softening starts at 124° C.).

Provenance & Evidence