Ethanol → HCID 58934612, compound

Participants

Reaction Steps

To a solution of the ester from Step 4 (250 mg, 0.713 mmole) in a 7:2:1 THF:EtOH:H2O mixture (10 mL) was added LiOH.H2O (44.9 mg, 1.07 mmole). The mixture was stirred room temperature for 15 minutes and then at 50° C. for 75 minutes. After standing at room temperature for 2.75 days, the solvent was removed in vacuo. The residue was redissolved in H2O (20 mL) and washed with ethyl ether (20 mL). The aqueous layer was concentrated to a volume of 5 mL and acidified with 1 N HCl. The resulting solid was filtered, washed with H2O and dried in vacuo to give 216 mg (94% yield) of the product as a yellow crystalline solid: ESHRMS m/z 321.0135 (M−H, C13H9ClF3O4, Calc'd 321.0136). 1H NMR (dmso-d6/300 MHz) 13.45 (brs, 1H), 7.88 (s, 1H), 7.13-7.16 (m, 2H), 6.02 (q, 1H, J=7.3 Hz), 4.03 (q, 2H, J=6.9 Hz), 1.32 (t, 3H, J=6.9 Hz).

Provenance & Evidence