2,2-Dimethoxypropane → HCID 58560662, compound

Participants

Reaction Steps

To a stirred mixture of Panaxytriol derivative (1R,7R,8R)-1-phenyl-2,4-pentadecadiyne-1,7,8-triol (12.8 mg, 39.0 μmol, 1.0 equiv) and 2,2-dimethoxypropane (40.6 mg, 390 μmol, 10 equiv) in dry THF (1.0 mL) was added p-TsOH.H2O (about 1 mg) at 0° C. The cooling bath was removed immediately and the mixture was stirred at room temperature. After 40 min, the reaction was quenched with a saturated solution of NaHCO3 (1 mL). The mixture was extracted with dichloromethane (4 times). The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude mixture was purified by gradient flash column chromatography (hexanes/EtOAc=9:18:17:1) to afford the title compound (14.0 mg, 97%) as a pale yellow oil: 1H-NMR (CDCl3, 400 MHz) δ 7.52-7.50 (m, 2H), 7.40-7.32 (m, 3H), 5.50 (s, 1H), 3.83-3.78 (m, 1H), 3.75-3.71 (m, 1H), 2.67-2.56 (m, 2H), 2.30 (br s, 1H), 1.68 (br s, 1H), 1.62-1.26 (m, 12H), 1.40 (s, 6H), 0.88 (t, J=7.0 Hz, 3H); 13C-NMR (CDCl3, 100 MHz) δ 139.75, 128.70, 128.62, 126.62, 108.72, 80.46, 78.11, 77.57, 75.53, 71.35, 66.51, 64.97, 32.90, 31.77, 29.62, 29.13, 27.40, 27.03, 25.94, 23.60, 22.62, 14.07.

Provenance & Evidence