(+-)-Pantolactone → HCID 59752169, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-4,4-dimethyldihydrofuran-2(3H)-one (4.5 g, 34.6 mmol), phenylmethanamine (5.66 mL, 51.9 mmol) and p-toluenesulfonic acid (0.595 g, 3.46 mmol) was sealed in a reaction vial and heated in microwave at 210° C. for 3 h. The mixture was diluted with ethyl acetate (300 mL). The organic layer was washed with 1N HCl (30 mL) three times, brine (20 mL), dried and concentrated. The residue was purified via silica gel chromatography, eluting with 20-50% ethyl acetate in hexanes, to give the title compound as a yellow oil (3.4 g, 45% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.37-7.29 (m, 3H), 7.26-7.22 (m, 2H), 4.55-4.36 (m, 2H), 4.02 (s, 1H), 3.37 (br. s., 1H), 3.00-2.83 (m, 2H), 1.18 (s, 3H), 0.96 (s, 3H); MS (ES+) m/z: 219.1, 220.1 (M+H); LC retention time: 2.83 min (analytical HPLC Method I).

Provenance & Evidence