Water → HCID 135973978, compound

Participants

Reaction Steps

A partially dissolved mixture of 64.5 g (0.155 mol) of 2-propionyl-3-hydroxy-5-(3-(5-(methylsulfonyl)-2-pyridyloxy)phenyl)cyclohex-2-en-1-one in 200 mL of CH2Cl2 and 700 mL of absolute ethanol was treated with 17.7 g (0.186 mol) of ethoxyamine hydrochloride and 15.3 g (0.186 mol) of sodium acetate. The resulting slurry was stirred for 20 hours at room temperature. The slurry was poured into 3 liters (L) of water and the CH2Cl2 layer was thoroughly removed. The CH2Cl2 layer was dried over MgSO4, filtered and the CH2Cl2 evaporated off to yield a pale oily residue. The residue was passed through a short column of silica gel (about 300 g), eluting with CH2Cl2. Evaporation of the initial 2 L of eluent afforded a pale oil. This oil was dissolved in 400 mL of diethyl ether which briefly formed a clear solution before precipitating the product as a white solid. The product was filtered and dried in vacuo to afford 63.5 g (89 percent of theoretical) of the above indicated product as a white crystalline solid. The product melted at 125.5°-128° C.; 1H NMR (CDCl3): δ1.17 (t, 3H, --N=CCH2CH3), 1.32 (t, 3H, --OCH2CH3), 2.68-3.62 (m includes s at 3.10, 10H, --N=CCH2 --, ring CH2CHCH2 --, CH3SO2 --), 4.18 (q, 2H, --OCH2 --), 7.05-7.58 (m, 5H, ArH's), 8.22 (dd, 1H, ArH), 8.78 (d, 1H, ArH), 15.1 (br s, 1H, enol H) (Compound 3).

Provenance & Evidence