Methanol → HCID 18385696, compound

Participants

Reaction Steps

A solution 10 g of 4-ethyl-4-hydroxy-1-{4-(methylthio)phenyl}-2-hexyn-1-one in 300 ml methanol was stirred in the presence of 4 ml diethylamine at room temperature for 12 hours. Then the solvent was removed in vacuo and the resulting residue was extracted with dilute aqueous HCl and dichloromethane (50 ml×3). The organic layer was washed with brine and then concentrated under reduced pressure to yield 5.6 g of 2,2-diethyl-5-{4-(methylthio)phenyl}-3(2H)-furanone. The crude product was used for the next step without further purification. NMR: δ0.85 (t, J=7.5 Hz, 6H), 1.88 (q, J=7.5 Hz, 4H), 2.54 (s, 3H), 5.96 (s, 1H), 7.31 (d, J=9.0 Hz, 2H), 7.75 (d, J=9.0 Hz, 2H). IR (cm−1): 2971, 1690, 1597, 1487, 1408, 1364, 1162, 1095.

Provenance & Evidence