Hydrochloric Acid → HCID 15702749, compound

Participants

Reaction Steps

To 230 mg of the ester from Step 1 in 3.0 mL of ethanol was added 2.2 mL of 0.5M aqueous LiOH and the resultant mixture heated at reflux for 8 h. The reaction mixture was then cooled to room temperature, poured into ethyl acetate and acidified with concentrated HCl. The organic layer was separated, washed with 1N HCl and brine (2x) and dried over MgSO4. Concentration gave a yellow oil which solidified on standing. Trituration with hexane gave the title compound. IR (KBr) 1710 cm-1. 'H NMR (CDCl3, 250 MHz) w 1.35-1.70 (m, 2H), 1.80-2.12 (m, 4H), 2.50-2.65 (m, H), 2.54 (d,d, J=6.5, 16.0 Hz, 1H), 2.72 (d,d, J=8.5 Hz, 1H), 2.95-3.06 (m, 1H), 3.46-3.58 (m, 1H), 5.28 (d, J=7.5 Hz, 1H), 5.43 (d, J=7.5 Hz, 1H), 6.80-6.92 (m, 1H), 6.83 (d, J=8.0 Hz, 2H), 7.26 (d,d, J=4.0, 9.0 Hz, 1H), 7.16 (d,d, J=2.5, 10.0 Hz, 1H), 7.21 (d, J=8.0 Hz, 2H).

Provenance & Evidence