Acetic Acid → HCID 67350119, compound

Participants

Reaction Steps

Potassium hydroxide (2.0 g) was added to a suspension of estrone (2.704 g, 10 mmol) and furfuraldehyde (2 mL, ca. 20 mmol) in ethanol (40 mL). The resulting dark brown solution was stirred for 4 hours at room temperature, then acetic acid (5 mL) and water (5 ml) were added. After a few minutes the product started to precipitate. The precipitation was completed by addition of more water (ca. 10 mL). The yellow solid was filtered off, washed with water, dissolved in chloroform and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was crystallised from ethyl acetate/hexane. Yield: 3.24 g (93%) light yellow crystals. 1H-NMR (CDCl3, 400 MHz) δ: 0.97 (s, 3H, —CH3), 1.42-1.76 (m, 5H), 2.00-2.20 (m, 2H), 2.22-2.35 (m, 1H), 2.36-2.51 (m, 2H), 2.82-3.00 (m, 2H), 3.14 (ddd, J=15.2, 6.6, 1.6 Hz, 1H), 5.08 (s, 1H, —OH),6.52 (dd, J=3.1, 1.6 Hz, 1H),6.62 (d, J=2.7 Hz, 1H),6.64-6.70 (m, 2H),7.16 (d, J=8.2 Hz, 1H), 7.22-7.27 (m, 1H), 7.57 (d, J=1.6 Hz, 1H). LRMS (FAB+): 349.2 (100, [M+H]+).

Provenance & Evidence